Hydrochloric Acid → 2-Fluoro-4-methylphenyl isothiocyanate

HRID 1008749Notes

Reaction equation

HRID 1008749 reaction equation
[C:1](Cl)(Cl)=[S:2].[F:5][C:6]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:7]=1[NH2:8].C(N(CC)CC)C.Cl>C(Cl)(Cl)Cl>[F:5][C:6]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:7]=1[N:8]=[C:1]=[S:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 679842-Fluoro-4-methylaniline

Product 1

HCID 27590302-Fluoro-4-methylphenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thiophosgen (4.0 mL) (supplied from Aldrich) was added dropwise to a solution of 2-fluoro-4-methylaniline (6.31 g) (supplied from Aldrich) in 70 mL of chloroform under ice cooling, and subsequently 15 mL of triethylamine was added dropwise thereto at the same temperature. The reaction solution was stirred at room temperature overnight. Then 70 mL of 1 N hydrochloric acid was added thereto, and the mixture was separated into two liquid phases. The organic layer was washed with 70 mL of water, dried on sodium sulfate anhydrate and subsequently concentrated The residue was applied onto the silica gel column and eluted with hexane, to yield 7.72 g of the title compound.

Workup

  1. customthe mixture was separated into two liquid phases
  2. washThe organic layer was washed with 70 mL of water
  3. customdried on sodium sulfate anhydrate
  4. concentrationsubsequently concentrated The residue
  5. washeluted with hexane

Sources & evidence

ORD record
ord-15855c07e4dc44bab118bb3abbf60819
Source dataset
uspto-grants-2011_07
Patent number
US07973030B2

Reaction notes

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