Sodium Carbonate → 2-Bromo-N-(4-chloro-2-(hydroxymethyl)phenyl)acetamide

HRID 72173Notes

Reaction equation

HRID 72173 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][OH:10].[Br:11][CH2:12][C:13](Br)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:11][CH2:12][C:13]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][OH:10])=[O:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 61147Bromoacetyl bromideHCID 5867542-Amino-5-chlorobenzyl alcohol

Product 1

HCID 866797092-Bromo-N-(4-chloro-2-(hydroxymethyl)phenyl)acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-amino-5-chlorophenyl)methanol (4.30 g, 27.3 mmol) in dichloromethane (220 ml) was added 2-bromoacetyl bromide (6.06 g, 2.61 ml, 30.0 mmol) at 0-5° C. Stirring for 5 minutes was followed by dropwise addition of aqueous 2 M sodium carbonate solution (130 ml) during approximately 10 minutes. The cooling bath was removed, and stirring was continued for 2 h. The solvent was removed in vacuo. The aqueous residue was extracted with three 100-ml portions of ethyl acetate. The combined organic layers were washed with one 50-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (7.30 g, 96%) as light grey solid, which was used in the next step without purification. MS m/e: 276 ([M+H]+).

Workup

  1. customThe cooling bath was removed
  2. stirringstirring
  3. waitwas continued for 2 h
  4. customThe solvent was removed in vacuo
  5. extractionThe aqueous residue was extracted with three 100-ml portions of ethyl acetate
  6. washThe combined organic layers were washed with one 50-ml portion of brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0eae883676b044c0a988453a6ab79790
Source dataset
uspto-grants-2014_09
Patent number
US08828989B2

Reaction notes

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