Bromine → Carbamic acid, [3-(bromoacetyl)phenyl]-, ethyl ester

HRID 236640Notes

Reaction equation

HRID 236640 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])[CH:9]=[CH:10][CH:11]=1)(=[O:5])[CH3:4]>O1CCOCC1.CCOCC>[Br:1][CH2:4][C:3]([C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])[CH:9]=[CH:10][CH:11]=1)=[O:5]

Participants

5

Reactant 2

HCID 24408BromineHCID 717681ethyl N-(3-acetylphenyl)carbamate

Product 1

HCID 20216369Carbamic acid, [3-(bromoacetyl)phenyl]-, ethyl esterYield 97.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

24.1 gm of bromine were added slowly over a period of 30 minutes to a stirred suspension of 28.5 gm of ethyl N-(3-acetyl-phenyl)-carbamate in 13.3 gm of dry dioxane and 245 ml of dry ether. After stirring the reaction solution for 2 hours more, it was cooled, and the product which crystallized out was collected and washed with ether, yielding 38.5 gm of the title compound, m.p. 108°-110° C.

Workup

  1. temperatureit was cooled
  2. customthe product which crystallized out
  3. customwas collected
  4. washwashed with ether

Sources & evidence

ORD record
ord-8e02b724a8734bcc9430caff2525a11b
Source dataset
uspto-grants-1987_02
Patent number
US04645841

Reaction notes

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