Thiophosgene → 2-Chloro-4-fluoro-1-isothiocyanatobenzene

HRID 1840385Notes

Reaction equation

HRID 1840385 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[N:4]=[C:10]=[S:11]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 75013Benzenamine, 2-chloro-4-fluoro-HCID 516892Sodium Bicarbonate

Product 1

HCID 27575812-Chloro-4-fluoro-1-isothiocyanatobenzeneYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Into a solution of 2-chloro-4fluoroaniline (500 mg, 3.44 mmol) in a mixture of chloroform and water (10 mL/10 mL) at room temperature, thiophosgene (0.53 mL, 6.88 mmol) and sodium bicarbonate (1.09 g, 10.32 mmol) were added. The mixture was stirred at room temperature for 16 hours. The mixture was partitioned between chloroform and water. The combined organic layer was then concentrated to give the desired product (586 mg, 91%). 1H NMR (CDCl3) δ 6.98 (m, 1H), 7.20 (m, 2H).

Workup

  1. customThe mixture was partitioned between chloroform and water
  2. concentrationThe combined organic layer was then concentrated

Sources & evidence

ORD record
ord-850af977e5ed43459636a528fdd35295
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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