Water → 4-Fluorophenylacetyl chloride

Into a 1-L three-neck flask equipped with a mechanical stirrer, an addition funnel, and a nitrogen bubbler vented to a water scrubber was placed 60.0 g (0.389 mol) of 4-fluorophenylacetic acid, 0.18 g, 0.002 mol) of N,N-dimethylformamide and 250 g of toluene. The addition funnel was charged with 50.4 g (0.397 mol) of oxalyl chloride and added to the reaction mixture over a 10 minute period resulting in gas evolution (4.7° C. exotherm was observed). The reaction mixture was stirred at ambient temperature for 2.5 hours (gas evolution complete) and the head space of the reaction flask was sparged with nitrogen for 10 minutes before storing the material. HPLC assay of the solution indicated that 19.1 wt % of the solution was 4-fluoroacetyl chloride, thus affording a 99% yield. Purification of crude 4-fluorophenylacetyl chloride by vacuum distillation (57-58° C., 0.15 mm Hg) affords 4-fluorophenylacetyl chloride as a clear liquid in 90% yield.

1. customInto a 1-L three-neck flask equipped with a mechanical stirrer, an addition funnel
2. additionadded to the reaction mixture over a 10 minute period
3. customresulting in gas evolution (4.7° C. exotherm was observed)
4. customthe head space of the reaction flask was sparged with nitrogen for 10 minutes
5. customthus affording a 99% yield
6. customPurification of crude 4-fluorophenylacetyl chloride
7. distillationby vacuum distillation (57-58° C., 0.15 mm Hg)

ORD record

ord-0c4f4e2a8198473380d2926977b08b20

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06713627B2