Methanol → (3-Bromo-5-fluorophenyl)methanol

To a suspension of 3-bromo-5-fluorobenzoic acid (4.51 g, 20.59 mmol) in THF (41.2 mL) at 0° C., BH3.THF (41.2 mL, 41.2 mmol) was added dropwise over 30 min, the reaction mixture was then allowed to return to room temperature and stirred at room temperature overnight. Methanol (40 mL) was added slowly and stirred at room temperature for 1 h. THF and Methanol was removed in vacuo. The residue was then extracted by EtOAc, and washed with sat.NaHCO3, The organic was dried and concentrated. The crude product was used in next step reaction without purification. LCMS (m/z): 187.2 (MH+−18), 0.66 min. 1H NMR (400 MHz, CDCl3) δ ppm 7.32 (s, 1H), 7.19-7.14 (m, 1H), 7.05 (tdd, J=0.7, 1.5, 9.1 Hz, 1H), 4.70 (br. s., 2H), 1.78 (br. s., 1H).

1. customto return to room temperature
2. stirringstirred at room temperature for 1 h
3. customTHF and Methanol was removed in vacuo
4. extractionThe residue was then extracted by EtOAc
5. washwashed
6. dry with materialNaHCO3, The organic was dried
7. concentrationconcentrated
8. customThe crude product was used in next step reaction without purification
9. custom187.2 (MH+−18), 0.66 min

ORD record

ord-ce263cb54f1843f780e6e27dc29f5c26

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242996B2