1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 16126823, compound

HRID 642797Notes

Reaction equation

HRID 642797 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[C:15]([C:23]([F:25])([F:24])[F:26])[CH:16]=2)=[O:22])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 27359133-Amino-5-fluorobenzotrifluoride

Product 1

HCID 16126823HCID 16126823, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Fluoro-5-trifluoromethyl-aniline (940 mg, 5.25 mmol, 1.05 eq.) in dry THF (20 ml) was added 4-Chloro-3-(trifluoromethyl)-phenylisocyanate (1.11 g, 5.0 mmol) at rt and the mixture was stirred overnight. Then it was diluted with cHexane (100 ml), washed twice with 2 N HCl, once with sat. NaHCO3 and brine (100 ml each) and adsorbed on Celite in vacuo. Flash chromatography on silica with cHexane/TBME (5:1 to 3:1) yielded 687 mg pure product (34%) as a white powder.

Workup

  1. additionThen it was diluted with cHexane (100 ml)
  2. washwashed twice with 2 N HCl, once with sat. NaHCO3 and brine (100 ml each)

Sources & evidence

ORD record
ord-9f0148fc15404ce09b19bc0709ff7a17
Source dataset
uspto-grants-2010_04
Patent number
US07696249B2

Reaction notes

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