3-Chloro-4-methylphenyl isocyanate → 4-Bromomethyl-3-chlorophenylisocyanate

HRID 1583483Notes

Reaction equation

HRID 1583483 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:9]=[C:10]=[O:11])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 628323-Chloro-4-methylphenyl isocyanateHCID 67184N-bromobutanimide

Product 1

HCID 135572724-Bromomethyl-3-chlorophenylisocyanateYield 100%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 100.0 grams (0.597 mole) of 3-chloro-4-methylphenylisocyanate in 1000 ml of carbon tetrachloride, under an argon atmosphere were added 116.8 grams (0.656 mole) of N-bromosuccinimide and 5.0 grams (0.021 mole) of benzoyl peroxide. The reaction mixture was warmed to reflux where it stirred for 4 hours; then it was allowed to cool to ambient temperature as it stood for 16 hours. The mixture was filtered and the filtrate concentrated under reduced pressure to give 147.1 grams of 4-bromomethyl-3-chlorophenylisocyanate as a residual oil. The oil was used without further purification.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux where it
  3. waitstood for 16 hours
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-57883c279b6642189f7f2c9595aa8581
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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