3-(3-BROMO-PHENYL)-PROPAN-1-OL

To a solution of 3-(3-bromophenyl)propionic acid (10.0 g, 43.7 mmol) in anhydrous THF (150 mL) was added 1.0 M BH3.THF (150 mL, 150 mmol) via addition funnel. After BH3.THF was added, the reaction was refluxed for 18 hrs. The reaction was quenched with water (100 mL) and 1N HCl (300 mL). The solution was saturated with sodium chloride and extracted with ethyl acetate. The organic extract was washed with brine and dried over magnesium sulfate. The organic material was purified by chromatography on silica gel eluting with ethyl acetate in hexane to produce 9.39 g (100percent) of the desired alcohol as a colorless oil. NMR (CDCl3) δ 1.82-1.89 (m, 2H), 2.67 (t, 2H), 3.64 (t, 2H), 7.11 7.15 (m, 1H), 7.29-7.31 (m, 1H), 7.34 (s, 1H).Part A. Preparation of: To a solution of 3-(3-bromophenyl)propionic acid (15.0 g, 65.5 mmol) in anhydrous THF (200 mL) at 5° C. was added, via addition funnel, 1.0 M BH3-THF (200 mL, 200 mmol). The reaction temperature was kept below 14° C. during the addition of the BH3THF. After all the BH3THF was added, the reaction was refluxed for 22 hr and then quenched with water (100 mL) and 1N HCl (300 mL). The solution was saturated with sodium chloride and extracted with ethyl acetate (3.x.300 mL). The organic extract was washed with brine, dried over magnesium sulfate, and concentrated providing 14.4 g (100percent) of crude alcohol as a colorless oil. NMR(CDCl3) δ 1.82-1.89 (m, 2H), 2.67 (t, 2H), 3.64 (t, 2H), 7.11-7.15 (m, 1H), 7.29-7.31 (m, 1H), 7.34 (s, 1H).Example 36. 3-(3-Bromo-plienvr)-propan-l-oI (23); [0173] 3-(3-Bromo-phenyl)-propionic acid (3.88 g, 16.9 mmol, 1 equiv) was diluted with THF (50 mL) and chilled to OInto a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(3-bromophenyl)propanoic acid (5 g, 21.83 mmol, 1.00 equiv) in THF (50 mL). This was followed by the addition of borane tetrahydrofuran complex solution (1 moL/L, 75 mL, 74.22 mmoL, 3.40 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The reaction mixture was poured into 150 mL of HCl (1 moL/L), extracted with 3×200 mL of DCM, washed with 300 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (10:1). The collected fraction was concentrated to afford 3-(3-bromophenyl)propan-1-ol (1.3 g, 28percent) as colorless oil. To a cooied (ice bath) soiution of 3-(3-bromophenyi)propanoic acid (8.0 g, 35 mmoi) in anhydrous THF (100 mL) was added BH3-THF (100 mL, 1.0 M) via addition funnei under a nitrogen atmosphere. The reaction was stirred at 0 °C for 1 h then at refiux for 16 h. The reaction was carefuiiy quenched with HCi (37 mL, 2 M) then concentrated to remove THF. The suspension was diiuted withDCM (300 mL) then fiitered to remove the soiids. The iayers were separatedand the organic phase was washed with water (50 mL) and brine (50 mL) then dried over anhydrous Na2SO4, filtered, and concentrated to give 3-(3-bromophenyl)propan-1-ol (9.8 g, >100percent) as a yellow oil, which was used for next step without further purification.To suspension Of LiAlHA solution of 1-allyl-3-bromobenzene (998 mg, 5.1 mmol) in THF (2 mL + 0.5 mL) was added to a solution of 9-BBN dimer (806 mg, 3.3 mol) in THF (6.6 mL). The mixture was stirred overnight at room temperature, then 3.0 M NaOH (2 mL) and 30percent H

Molecular Weight:215.09
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:213.99933
Monoisotopic Mass:213.99933
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:106
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes