Bromine → N-(4-Bromo-3-chloro-2-methylphenyl)acetamide

HRID 2171590Notes

Reaction equation

HRID 2171590 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:13]Br>CC(O)=O>[Br:13][C:7]1[CH:6]=[CH:5][C:4]([NH:8][C:9](=[O:11])[CH3:10])=[C:3]([CH3:12])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 81969N-(3-chloro-2-methylphenyl)acetamide

Product 1

HCID 86376N-(4-Bromo-3-chloro-2-methylphenyl)acetamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of N-(3-chloro-2-methylphenyl)acetamide (35 g, 0.19 mol) in 350 mL of glacial AcOH cooled to 0° C. was added bromine (29.5 mL, 0.57 mol) dropwise. The ice bath was removed and the solution was stirred for 24 h and then poured into ice water with stirring. The solid was then filtered and dried to give the title compound (45 g, 90%) which was used for the next step without any further purification.

Workup

  1. customThe ice bath was removed
  2. additionpoured into ice water
  3. stirringwith stirring
  4. filtrationThe solid was then filtered
  5. customdried

Sources & evidence

ORD record
ord-ddce93e5c3684f728fa4023a9286477c
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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