Water → 4-(Chloro(hydroxyimino)methyl)-2-trifluoromethyl-benzoic acid methyl ester

HRID 467938Notes

Reaction equation

HRID 467938 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[N:11][OH:12])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14].[Cl:18]N1C(=O)CCC1=O.O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([Cl:18])=[N:11][OH:12])=[CH:6][C:5]=1[C:13]([F:15])([F:14])[F:16]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 723270974-(Hydroxyimino-methyl)-2-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 723270954-(Chloro(hydroxyimino)methyl)-2-trifluoromethyl-benzoic acid methyl esterYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(hydroxyimino-methyl)-2-trifluoromethyl-benzoic acid methyl ester (Example I11) (3.90 g) in N,N-dimethylformamide (20 ml) was added N-chlorosuccinimide (“NCS”) (2.318 g). The reaction mixture was stirred at ambient temperature for 45 minutes. The reaction mixture was poured into water (400 ml). The solids were isolated by filtration and dried to give 4-(chloro(hydroxyimino)methyl)-2-trifluoromethyl-benzoic acid methyl ester (4.21 g) as an off-white powder. 1H-NMR (CDCl3, 400 MHz): 9.00 (s, 1H), 8.24-8.04 (m, 3H), 3.96 (s, 3H).

Workup

  1. customThe solids were isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-3b6b2fd00a0843b7897dd89fe363b06b
Source dataset
uspto-grants-2014_01
Patent number
US08623896B2

Reaction notes

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