3-Bromoaniline → phenyl N-(3-bromophenyl)carbamate

HRID 2166533Notes

Reaction equation

HRID 2166533 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>CCOCC>[Br:11][C:12]1[CH:13]=[C:14]([NH:15][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 15891Phenyl chloroformate

Product 1

HCID 885442phenyl N-(3-bromophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.56 g. of phenyl chloroformate in 50 ml. of ether is added dropwise to a stirred solution of 3.44 g. of 3-bromoaniline in 35 ml. of ether, the mixture is stirred for one hour at room temperature and then filtered. The filtrate is evaporated and the residue is crystallized from hexane to yield phenyl N-(3-bromophenyl)carbamate, m.p. 88°-90° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. customthe residue is crystallized from hexane

Sources & evidence

ORD record
ord-5773309338d94b81b3ede042ef266d68
Source dataset
uspto-grants-1983_06
Patent number
US04387106

Reaction notes

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