Acetic Anhydride → 4'-Bromo-2'-(trifluoromethyl)acetanilide

HRID 53769

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[C:13]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([F:12])([F:10])[F:11])(=[O:15])[CH3:14]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 679604-Bromo-2-(trifluoromethyl)aniline

Product 1

HCID 27734174'-Bromo-2'-(trifluoromethyl)acetanilideYield 99.7%

Procedure

A solution of 2-amino-5-bromobenzotrifluoride (1.623 g, 6.76 mmol, Aldrich) in acetic anhydride (10 mL) was stirred at room temperature for 12 h to produce a white needle precipitate. It was filtered to give 1.840 g (99.7%) of title compound. Mp: 140°-2° C., 1HNMR (CDCl3): δ 2.212 (s, 3H); 7.358 (s, 1H); 7.659 (d, 1H, J =8.7 Hz); 7.726 (d, 1H, J=1.8 Hz); 8.118 (d, 1H, J=8.4 Hz).

Workup

customto produce a white needle precipitate
filtrationIt was filtered

Sources & evidence

ORD record: ord-a8f3fd9bf59a4c7c9c40d591d3b3323c
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620979

Linked notes

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