2-Fluoro-3-methoxybenzoic acid → 2-Fluoro-3-methoxybenzyl alcohol

2-Fluoro-3-methoxybenzoic acid from Step 1 (16.65 g, 98 mmol) was dissolved in anhydrous tetrahydrofuran (60 mL), cooled in an ice bath, and treated with borane dimethyl sulfide complex (19 mL, 190 mmol). The reaction was stirred at room temperature for 4.2 hours, quenched by the slow addition of methanol, and concentrated in vacuo. The residue was dissolved in ethyl acetate, treated with 3N hydrochloric acid and filtered through diatomaceous earth. The organic layer of the filtrate was collected, washed with NaHCO3, brine, dried over MgSO4 and reconcentrated in vacuo to give 2-fluoro-3-methoxybenzyl alcohol (12.35 g, 81%) as a white solid: mp 53°-57° C.; 1H NMR (acetone-d6) 300 MHz 7.07 (m, 3H) 4.67 (d, J=5.8 Hz, 2H) 4.24 (t, J=5.8 Hz, 1H) 3.86 (s, 3H); 19F NMR (acetone-d6) 300 MHz -144.77(m).

1. temperaturecooled in an ice bath
2. additiontreated with borane dimethyl sulfide complex (19 mL, 190 mmol)
3. customquenched by the slow addition of methanol
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was dissolved in ethyl acetate
6. additiontreated with 3N hydrochloric acid
7. filtrationfiltered through diatomaceous earth
8. customThe organic layer of the filtrate was collected
9. washwashed with NaHCO3, brine
10. dry with materialdried over MgSO4

ORD record

ord-925c1615e9ee465c9a58be539452f34e

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05670532