Thiophosgene → 2,6-Difluorophenyl isothiocyanate

HRID 2244393Notes

Reaction equation

HRID 2244393 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(N(C(C)C)CC)(C)C>ClCCl>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[N:4]=[C:10]=[S:11]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 796472,6-DifluoroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 40316012,6-Difluorophenyl isothiocyanateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Difluoro-2-isothiocyanato-benzene was synthesized as follows, according to scheme 1. A solution of 2,6-difluoro aniline (0.13 g, 1.01 mmol) in dichloromethane (10.00 ml) was treated with thiophosgene (0.12 g, 1.06 mmol) and diisopropylethylamine (0.26 g, 2.01 mmol). The mixture was stirred for 1 h at room temperature. The solvent was then evaporated, leaving 1,3-difluoro-2-isothiocyanato-benzene (0.17 g, 99%) as a light brown gum, which was used crude.

Workup

  1. custom1,3-Difluoro-2-isothiocyanato-benzene was synthesized
  2. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-45a270330e544e6dbf76c6e60460c119
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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