Water → 2-bromo-N-(4-methoxy-2-nitrophenyl)acetamide

HRID 651374Notes

Reaction equation

HRID 651374 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH3:6][O:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1.C(N(CC)CC)C.O>C(Cl)Cl>[Br:1][CH2:2][C:3]([NH:12][C:11]1[CH:13]=[CH:14][C:8]([O:7][CH3:6])=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 45865232-bromo-N-(4-methoxy-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-bromoacetylbromide (17.9 ml; 0.20 moles) in CH2Cl2 (30 ml) was slowly added to a mixture of 4-methoxy-2-nitroaniline (30 g; 0.18 moles) and triethylamine (28 ml; 0.2 moles) in CH2Cl2 (300 ml). The reaction mixture was stirred at room temperature overnight, then poured into water. The aqueous layer was extracted with additional CH2Cl2, dried over MgSO4 and evaporated under vacuum. The crude product was crystallized from a 7/3 Et2O/EtOH mixture to give the title compound as a white solid. 31.5 g; m.p. 94-98° C.

Workup

  1. extractionThe aqueous layer was extracted with additional CH2Cl2
  2. dry with materialdried over MgSO4
  3. customevaporated under vacuum
  4. customThe crude product was crystallized from a 7/3 Et2O/EtOH mixture

Sources & evidence

ORD record
ord-06ebbdbc6d064f22a54a4c6c0a3ef007
Source dataset
uspto-grants-2001_08
Patent number
US06281218B1

Reaction notes

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