Yield:18349-09-2 98%

Reaction Conditions:

with N-Bromosuccinimide in acetic acid at 15 - 20; for 1.66667 h;

Steps:

31

A stirred solution of 4-methyl-2-fluoroaniline (15g, 0.12 mol) in acetic acid (120ml) at 15⁰C under argon was treated portionwise over 20 minutes with solid N-bromosuccinimide (24g, 0.135 mol), then allowed to warm to room temperature and stirred for 1 hr. The reaction mixture was treated with water (500ml) and extracted with ethyl acetate (2 x 300ml). The combined extract was washed with water (2 x 500ml), then excess 10% Na₂CO₃ solution (400ml). The ethyl acetate solution was dried (Na₂SO₄) and concentrated under vacuum to leave the title compound as a dark red oil (24.Og, 98%). ¹H NMR δ (CDCI₃, 400MHz): 2.22 (3H, s), 3.95 (2H, br s), 6.78 (1H, d), 7.02 (1H, s).

References:

WO2007/36715,2007,A2 Location in patent:Page/Page column 54-55