Pivaloyl chloride → N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamide

Participants

Reaction Steps

Trimethylacetyl chloride (0.25 mL, 1.99 mmol) was added to a solution of (2-amino-6-fluorophenyl) methanol (268 mg, 1.90 mmol) in CH2Cl2 (10 mL) at 0° C., followed by the addition of DIEA (1.0 mL, 5.7 mmol). The mixture was stirred for 1 hr, followed by normal aqueous work-up to afford the expected crude product, N-(3-fluoro-2-(hydroxymethyl)phenyl)pivalamide, as a colorless oil (415 mg, 97% yield), which was used directly in the next step; 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (s, 9 H), 2.64 (s, 1 H), 4.78 (d, J=4.78 Hz, 2 H), 6.75-6.84 (m, 1 H), 7.23 (td, J=8.62, 5.92 Hz, 1 H), 7.86 (d, J=8.31 Hz, 1 H), 8.97 (s, 1 H); Mass spec. 226.11 (MH+), Calc. for C12H16FNO2 225.12.

Provenance & Evidence