2-Bromothiophene → HCID 95003689, compound

Participants

Reaction Steps

To a solution of 2-bromothiophene (0.95 mL, 9 mmol) in ether (60 mL) cooled to −100° C. was added t-butyl lithium (5.41 mL of 1.7 M in pentane, 9 mmol) by dropwise addition. The reaction mixture was stirred at this temperature for 30 min. (R)-Epichlorohydrin (1.08 mL, 14 mmol) was added and the −100° C. bath was replaced with an ice/ethanol bath. The reaction was stirred at this temperature for 1.5 h and then stirred in an ice-bath for an additional 1.5 h. The reaction mixture was poured onto water and extracted with EtOAc (3 times). The combined organic phases were washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography (50% EtOAc in heptane eluent) to afford (R)-1-chloro-3-thiophen-2-yl-propan-2-ol (410 mg, 25%) as a brown oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.28 (d, J=4.14 Hz, 1H) 3.06-3.21 (m, 2H) 3.46-3.73 (m, 2H) 4.08 (d, J=5.65 Hz, 1H) 6.91 (dd, J=3.39, 0.94 Hz, 1H) 6.98 (dd, J=5.09, 3.39 Hz, 1H) 7.21 (dd, J=5.18, 1.22 Hz, 1H).

Provenance & Evidence