Triethylamine → 3-Chloro-2-fluorophenylisothiocyanate

HRID 1840356Notes

Reaction equation

HRID 1840356 reaction equation
[F:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(N(CC)CC)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[F:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]=[C:10]=[S:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10040ThiophosgeneHCID 750143-Chloro-2-fluoroaniline

Product 1

HCID 27575833-Chloro-2-fluorophenylisothiocyanateYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Into a solution of 2-fluoro-3-chloroaniline (1.0 g, 6.87 mmol) in 30 mL of toluene at room temperature, thiophosgene (0.8 mL, 10.3 mmol) and triethylamine (1.12 mL, 8.24 mmol) were added. The mixture was stirred at room temperature for 16 hours. The mixture was parationed between ethyl acetate and water. The combined organic layer was then concentrated to give the desired product (950 mg, 74%). 1H NMR (CDCl3) δ 7.09 (m, 2H), 7.30 (m, 1H).

Workup

  1. concentrationThe combined organic layer was then concentrated

Sources & evidence

ORD record
ord-68cb9c62588f4f9db7166c3fd3d9f919
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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