Methanol → (5-Bromo-2-chlorothiophen-3-yl)methanol

Temperature

0 °C

To a solution of acid 1 (3.0 g, 12.4 mmol) in THF (50 mL) were added borane dimethylsulfide complex (10M in THF, 3.2 mL, 31.1 mmol) at 0° C. The mixture was stirred at 0° C. for 15 min, at room temperature for 45 min, and at 65° C. for 2 hours. The reaction mixture was cooled to 0° C. To the mixture were added MeOH (30 mL), H2O (250 mL) dropwise at 0° C. The mixture was extracted with EtOAc (100 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to obtain the title compound 31 (2.8 g, 99%). The crude alcohol 31 was carried on to the next step without further purification.

1. waitat 65° C. for 2 hours
2. temperatureThe reaction mixture was cooled to 0° C
3. extractionThe mixture was extracted with EtOAc (100 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-adf4f30a26f14787a65a0f0c1462f7b0

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006187B2