(2-Bromothien-3-yl)methanol

To a solution of 3-hydroxymethylthiophene 12 (4.06 g, 35.6 mmol) in 18 mL of acetic acid was added N-bromosuccinimide (6.34 g, 35.6 mol) at room temperature and stirred for 45 minutes. The resulting mixture was quenched with 1 mL of water, poured into 250 mL ether and washed with 100 mL of water, 100 mL of 10percent NAHC03 aq. respectively. The organic layer was dried over NA2S04 and concentrated. 6.25 G of crude product 13 (91 percent) was obtained and used for the subsequent reaction without further purification.According to the reported procedure, The compound in the title was synthesized according to the following modified literature procedure.16 A flame-dried 100 mL Schlenk tube was filled with argon and then charged with PdCl2(PPh3)2 (0.182 g, 0.257 mmol), CuI (30.6 mg, 0.160 mmol) and i-Pr2NH (20 mL). After degassing by three freeze-thaw cycles, 2-Bromo-3-hydroxymethylthiophene (13). To a solution of 3-hydroxymethylthiophene 12 (4.06 g, 35.6 mmol) in 18 mL of acetic acid was added N-bromosuccinimide (6.34 g, 35.6 mol) at room temperature and stirred for 45 minutes. The resulting mixture was quenched with 1 mL of water, poured into 250 mL ether and washed with 100 mL of water, 100 mL of 10% NaHCO3 aq. respectively. The organic layer was dried over Na2SO4 and concentrated. 6.25 g of crude product 13 (91%) was obtained and used for the subsequent reaction without further purification. 2-Bromo-3-(tert-butyldimethylsiloxymethyl)thiophene (14).This crude product was dissolved in tetrahydrofuran (50 ml), and 1N aqueous sodium hydroxide (50 ml) and ethanol (20 ml) were added. The mixture was stirred at room temperature for 2 hours and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crude product of To a solution of This crude product of A solution of 10.0 g (39.0 mmol) of 2-bromo-3-bromomethyl-thiophene (J Chem. Soc Perkin Trans. II, 1983:813) in 130 mL of acetone was treated with a solution of 11.4 g (67.1 mmol) of AgNO3 in 110 mL of H2O. The mixture was stirred at room temperature for 1 hour and filtered. The solid was washed with Et2O and acetone; the combined filtrate and washings were concentrated. The residue was extracted with CH2Cl2, and the organic layer was dried (MgSO4) and concentrated. The crude product was chromatographed over silica gel, eluding with hexane:EtOAc:CH2Cl2 (80:5:15 to 60:30:10) to give the title compound. 1H NMR (CDCl3) delta1.67 (t, 1 H), 4.63 (d, 2 H), 7.03 (d, 1 H), 7.26 (d, 1 H).

Molecular Weight:193.06
XLogP3:1.7
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