Acetyl chloride → Methyl 5-acetamido-2-bromobenzoate

HRID 871959Notes

Reaction equation

HRID 871959 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>ClCCl>[C:20]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([Br:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 245495Methyl 5-amino-2-bromobenzoate

Product 1

HCID 58891822Methyl 5-acetamido-2-bromobenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 5-amino-2-bromobenzoate (Reference Compound No. 1-(1), 21.0 g, 91.2 mmol) was dissolved in anhydrous dichloromethane (450 mL), triethylamine (19.0 mL, 137 mmol) and acetyl chloride (13.0 mL, 182 mmol) were added dropwise over 30 minutes successively, and then the mixture was stirred at 0° C. for 2 hours. The reaction mixture was washed with water (200 mL, 2 times), saturated aqueous sodium hydrogen carbonate solution (200 mL, 2 times), and saturated brine (200 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was filtered with hexane-ethyl acetate (20:1) to give the titled reference compound (24.2 g) as a pale yellow solid. (Yield 98%)

Workup

  1. washThe reaction mixture was washed with water (200 mL, 2 times), saturated aqueous sodium hydrogen carbonate solution (200 mL, 2 times), and saturated brine (200 mL) successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. filtrationThe obtained residue was filtered with hexane-ethyl acetate (20:1)

Sources & evidence

ORD record
ord-4c8ed155e9e14899836e0c1be4cb74e6
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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