Water → (4-Bromo-2-chlorophenyl)methanol

Temperature

0 °C

4-Bromo-2-chlorobenzoic acid (5 g, 21.23 mmol) was dissolved in dry THF (100 mL) and cooled to 0° C. A 1M solution of BH3.THF in THF (31.85 mL, 31.85 mmol) was slowly added. The reaction was stirred overnight, allowing it to gradually reach room temperature. K2CO3 solid (1 g) and H2O (100 mL) were added and the reaction was stirred for 30 minutes. THF was evaporated and residue extracted with EtOAc (30 mL). The organic phase was washed with 1N HCl (3×50 mL), brine (3×50 mL), dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography (30% EtOAc in hexanes) to give the product (2.80 g, 50%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 4.73 (d, J=5.8 Hz, 2H), 7.37 (d, J=8.1 Hz, 1H), 7.42 (dd, J=8.1 Hz, 1.7), 7.52 (d, J=1.7 Hz, 1H)

1. customto gradually reach room temperature
2. stirringthe reaction was stirred for 30 minutes
3. customTHF was evaporated
4. extractionresidue extracted with EtOAc (30 mL)
5. washThe organic phase was washed with 1N HCl (3×50 mL), brine (3×50 mL)
6. dry with materialdried over Na2SO4
7. customevaporated
8. customThe residue was purified by flash column chromatography (30% EtOAc in hexanes)

ORD record

ord-c0ab4c0d5f674895bc65332e5d976024

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2