Acetic Anhydride → N-(3-Bromophenyl)acetamide

HRID 250876Notes

Reaction equation

HRID 250876 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[Br:8][C:9]1[CH:10]=[C:11]([NH:12][C:5](=[O:7])[CH3:6])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 115623-Bromoaniline

Product 1

HCID 12123N-(3-Bromophenyl)acetamideYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

691 mL of acetic anhydride are added to a solution cooled to 10° C. of 1200 g (6.976 mol, 1 eq) of 3-bromoaniline in 6 L of dichloromethane in the presence of 1.07 L (7.67 mol, 1.1 eq) of triethylamine and 25.6 g (0.209 mol, 0.03 eq) of 4-(dimethylamino)pyridine. The reaction medium is stirred at room temperature for 4 hours and then hydrolyzed with 850 mL of 1N hydrochloric acid solution, and the phases are separated by settling. The organic phase is washed with 0.5N hydrochloric acid solution and then with water, and the solvent is evaporated off. After recrystallization from diisopropyl ether/heptane, 1506.1 g of N-(3-bromophenyl)acetamide are obtained in solid form. Yield=100%

Workup

  1. customhydrolyzed with 850 mL of 1N hydrochloric acid solution, and the phases are separated
  2. washThe organic phase is washed with 0.5N hydrochloric acid solution
  3. customwith water, and the solvent is evaporated off
  4. customAfter recrystallization from diisopropyl ether/heptane, 1506.1 g of N-(3-bromophenyl)acetamide
  5. customare obtained in solid form

Sources & evidence

ORD record
ord-02641fcbaacd41349abdd2e50b713709
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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