Triethylamine → 3-fluoro-2-methylphenylisothiocyanate

HRID 1840374Notes

Reaction equation

HRID 1840374 reaction equation
[CH3:1][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>[CH3:1][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 2855533-Fluoro-2-methylaniline

Product 1

HCID 27590323-fluoro-2-methylphenylisothiocyanateYield 82.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 2-methyl-3-fluoroaniline (1.0 g, 8.0 mmol) in 30 mL of toluene at room temperature, thiophosgene (0.94 mL, 12 mmol) and triethylamine (1.34 mL, 12 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 (1.1 g, 82%). EI-MS m/z 168.2 (M+).

Workup

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

Sources & evidence

ORD record
ord-29631824a64d4a1494f487d135d9e8d5
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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