Triethylamine → 2-Fluorophenyl isothiocyanate

HRID 1840365Notes

Reaction equation

HRID 1840365 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9](Cl)(Cl)=[S:10].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]=[C:9]=[S:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95842-FluoroanilineHCID 10040Thiophosgene

Product 1

HCID 975202-Fluorophenyl isothiocyanateYield 76.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 2-fluoroaniline (1.0 g, 9.0 mmol) in 30 mL of toluene at room temperature, thiophosgene (1.06 mL, 13.5 mmol) and triethylamine (1.55 mL, 13.5 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 (1.05 g, 76%). 1H NMR (CDCl3) δ 7.1-7.3 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-838f4f59cde64a41b9bfd9572e39d80b
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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