Acetic Anhydride → N-(2-bromobenzyl)acetamide

HRID 2194875Notes

Reaction equation

HRID 2194875 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH2:10].C(N(CC)CC)C.[C:18](OC(=O)C)(=[O:20])[CH3:19]>C(Cl)Cl.Cl>[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][C:18](=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 27242022-Bromobenzylamine hydrochloride

Product 1

HCID 2824953N-(2-bromobenzyl)acetamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of commercially available 1-(2-bromophenyl)methanamine hydrochloride salt (1 eq.) in CH2Cl2 (0.3M) at room temperature was added triethylamine (2.1 eq) then acetic anhydride (1.1 eq.). The mixture was stirred at room temperature for 6 h, poured in aqueous HCl (0.5N) and extracted with CH2Cl2. The organic extract was dried over MgSO4 filtered and concentrated to afford the desired compound as a white solid.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-22f476d86f1f4adb86906ea5f18b2b69
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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