Triethylamine → 1,2-difluoro-3-isothiocyanatobenzene

HRID 1840369Notes

Reaction equation

HRID 1840369 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(Cl)=[S:11].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]=[C:10]=[S:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 782782,3-Difluoroaniline

Product 1

HCID 27583301,2-difluoro-3-isothiocyanatobenzeneYield 68.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 2,3-difluoroaniline (1.0 g, 7.74 mmol) in 30 mL of toluene at room temperature, thiophosgene (0.91 mL, 11.6 mmol) and triethylamine (1.3 mL, 11.6 mmol) was added. The mixture was stirred at room temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The combined organic layer was then concentrated to give the desired product (910 mg, 68%). 1H NMR (CDCl3) δ 6.98 (m, 2H), 7.11 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-4bc40e1f9de54afe803912eae42780a0
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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