Thiophosgene → 2-Fluoro-1-isothiocyanato-3-trifluoromethyl-benzene

HRID 645567

Reaction equation

HRID 645567 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:12].C(=O)(O)[O-].[Na+].[C:18](Cl)(Cl)=[S:19]>ClCCl.O>[F:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:12]=[C:18]=[S:19]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 1455693-Amino-2-fluorobenzotrifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 834024072-Fluoro-1-isothiocyanato-3-trifluoromethyl-benzeneYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a two phase solution of 2-fluoro-3-trifluoromethyl-phenylamine (2 g, 11.17 mmole) in dichloromethane (40 ml) and sodium bicarbonate (6.57 g, 78.19 mmole) in water (30 ml) at 0° C. was added dropwise a solution of thiophosgene (1.28 g, 11.17 mmole) in dichloromethane (10 ml). After 2 hrs, the organic layer was separated, washed sequentially with 1M NaHCO3, brine and water. The organic layer was dried over Na2SO4, filtered and concentrated to yield 2.2 g (91%) of product as a viscous liquid. MS (ESI+) m/z 221 (M+H)+.

Workup

  1. customthe organic layer was separated
  2. washwashed sequentially with 1M NaHCO3, brine and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf0ee22f5cc94cfc926380c79a751eaf
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Linked notes

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