Dimethylformamide → 2-(4-Cyano-2-fluoro-phenoxymethyl)-benzoyl chloride

HRID 1875771Notes

Reaction equation

[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][CH2:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11](O)=[O:12])=[C:5]([F:20])[CH:4]=1)#[N:2].C(Cl)(=O)C([Cl:24])=O.CN(C)C=O>ClCCl>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][CH2:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([Cl:24])=[O:12])=[C:5]([F:20])[CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 2-(4-cyano-2-fluoro-phenoxymethyl)-benzoic acid (1.0 g, 3.68 mmol) in dichloromethane (15 ml) was added oxalyl chloride (0.45 ml, 4.79 mmol), followed by a drop of N,N-dimethylformamide, and stirred for 12 h at 25° C. The resulting clear solution was evaporated in vacuo and the crude product was used in the next step without any further purification (99%). MS (Turbo Spray): m/z=290.1 (M+H).

Workup

customThe resulting clear solution was evaporated in vacuo
customthe crude product was used in the next step without any further purification (99%)

Sources & evidence

ORD record: ord-380d637c91bf427e90260c6a7934c9ee
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309581B2

Reaction notes

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