Phosgene → 3,4-Difluorophenyl isocyanate

HRID 66439

Reaction equation

HRID 66439 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].ClC1C2C(=CC=CC=2)C=CC=1.[C:21](Cl)(Cl)=[O:22]>>[F:1][C:2]1[CH:3]=[C:4]([N:5]=[C:21]=[O:22])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

4

Reactant 3

HCID 6371Phosgene3×HCID 70031-ChloronaphthaleneHCID 774693,4-Difluoroaniline

Product 1

HCID 27347083,4-Difluorophenyl isocyanate

Conditions

Temperature
150 °C

Procedure

At -10° to 0° and while stirring, 120 g of 3,4-difluoroaniline (J. Chem. Soc., 73, 5884-5, 1951) is metered into a solution of 180 parts by weight of phosgene in 1,100 parts by weight of chloronaphthalene. The reaction mixture is then slowly heated to 150° C. while passing in additional phosgene, and phosgenated for 2 hours at this temperature. Excess phosgene is expelled with nitrogen and the isocyanate distilled from the solution; b.p. (30 mm Hg): 79°-85° C.

Workup

  1. distillationthe isocyanate distilled from the solution
  2. custom79°-85° C.

Sources & evidence

ORD record
ord-0948dd6266ce475dbffc5549c083ee48
Source dataset
uspto-grants-1978_12
Patent number
US04131751

Linked notes

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