3-Bromo-2-thiophenemethanol

To a solution of 3- bromothiophene-2-carbaldehyde (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 firs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.[00473] To a solution of 3-bromothiophene-2-carbaldehyde (6) (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 hrs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.A/Preparation of 3-Bromo-2-hydroxymethyl-thiophene: b. To a solution of 3- bromothiophene-2-carbaldehyde (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 firs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.[00473] To a solution of 3-bromothiophene-2-carbaldehyde (6) (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 hrs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.Stirring of 3-bromothiophene-2-carboxaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) at 0 ° C under argon, and adding sodium borohydride (NaBH 4 , 3.4 g, 90.1 mmol) and stirred at room temperature for 24 hours. An aqueous solution of ammonium chloride was added to the oily solid obtained by concentration of the reaction mixture under reduced pressure, and the organic layer was extracted with ethyl acetate. After the extract was dried over magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure to give a crude material. The crude product was purified by a silica gel column chromatography (ethyl acetate / hexane (volume ratio) = 2 / 8) to thereby obtain 3-bromothiophene-2-methanol (the compound (3-1), The yield was 9.3 g, and the yield was 92percent)A solution of 3-bromothiophene-2-carboxaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) was stirred at 0 ° C under an argon atmosphere, and sodium borohydride (NaBH 4 , 3.4 g, 90.1 mmol) and stirred at room temperature for 24 hours. An aqueous solution of ammonium chloride was added to the obtained oily solid, and the organic layer was extracted with ethyl acetate. After the extract was dried over magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure to give a crude material. The crude product was purified by silica gel column chromatography (ethyl acetate / hexane (volume ratio) = 2/8), whereby 3-bromothiophene-2-methanol (the compound (3) -1), yield 9.3 g, yield 92percent).In an argon environment, A solution of 3-bromothiophene-2-carbaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) was stirred at 0 ° C.Sodium borohydride (NaBH4, 3.4 g, 90.1 mmol) was added on one side.Stir at room temperature for 24 hours.The oily solid obtained by concentrating the reaction liquid under reduced pressure is added to an aqueous solution of ammonium chloride.The organic layer was extracted with ethyl acetate.Drying the extract with magnesium sulfate, After filtering, The filtrate was concentrated under reduced pressure to give a crude product.The crude product was purified by column chromatography (ethyl acetate/hexane (volume ratio) = 2/8).And the target compound 3-bromothiophene-2-methanol was obtained.(Compound (3-1), yield 9.3 g, yield 92percent).A/Preparation of 3-Bromo-2-hydroxymethyl-thiophene: b.

Molecular Weight:193.06
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:191.92445
Monoisotopic Mass:191.92445
Topological Polar Surface Area:48.5
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes