2-(2-Bromo-5-chlorophenyl)acetic acid → 2-(2-Bromo-5-chlorophenyl)ethanol

A solution of 2-(2-bromo-5-chloro-phenyl)acetic acid (1.00 g, 4.01 mmol) in THF (16 mL) was cooled to 0° C. Borane-tetrahydrofuran complex (6.0 mL, 62.69 mmol) was added and the solution allowed to warm to room temperature and stirred for 3 h. Another portion of borane-tetrahydrofuran complex (6.0 mL, 62.69 mmol) was added and the reaction stirred overnight. The reaction was cooled to 0° C. and quenched by the careful addition of cold water. The aqueous was extracted with EtOAc and the organic layer washed with 2M HCl, dried (Na2SO4), and concentrated. The material was dissolved in DCM and PS-DEAM (1 g) was added and stirred overnight. The resin was filtered washing with DCM and concentrated to afford 2-(2-bromo-5-chlorophenyl)ethanol as an oil (944 mg, quant). 1H NMR (500 MHz, CDCl3) δ 7.40 (1H, d), 7.30 (1H, s), 7.00-7.03 (1H, m), 3.80-3.84 (2H, m), 2.91-2.94 (2H, m).

1. additionBorane-tetrahydrofuran complex (6.0 mL, 62.69 mmol) was added
2. additionAnother portion of borane-tetrahydrofuran complex (6.0 mL, 62.69 mmol) was added
3. stirringthe reaction stirred overnight
4. temperatureThe reaction was cooled to 0° C.
5. customquenched by the careful addition of cold water
6. extractionThe aqueous was extracted with EtOAc
7. washthe organic layer washed with 2M HCl
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated
10. dissolutionThe material was dissolved in DCM
11. additionPS-DEAM (1 g) was added
12. stirringstirred overnight
13. filtrationThe resin was filtered
14. washwashing with DCM
15. concentrationconcentrated

ORD record

ord-117cbda84e5044c1a0f931f9f589c8f8

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073875B2