Potassium Carbonate → 4-(2-Acetoxy-ethoxy)-3-bromo-5-fluoro-benzoic Acid Methyl Ester

HRID 1918338Notes

Reaction equation

HRID 1918338 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[C:6]([Br:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[C:20]([O:23][CH2:24][CH2:25]Br)(=[O:22])[CH3:21]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH2:25][CH2:24][O:23][C:20](=[O:22])[CH3:21])=[C:6]([Br:12])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 57467610HCID 57467610, compound

Product 1

HCID 671706184-(2-Acetoxy-ethoxy)-3-bromo-5-fluoro-benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-5-fluoro-4-hydroxybenzoic acid methyl ester (500 mg, 2.01 mmol; T. Kline et al., J. Med. Chem. 45 (2002), 3112-3129), potassium carbonate (971 mg, 7.03 mmol) and 2-bromoethyl acetate (503 mg, 3.01 mmol) were reacted in DMF (5 ml) at room temperature for 72 h. Then the mixture was partitioned between EA and 2 N hydrochloric acid, and the combined organic extracts were dried over sodium chloride, decanted and evaporated to dryness. The raw material was purified by silica gel chromatography (EA/HEP gradient 0:1 to 4:6) to yield the title compound.

Workup

  1. customThen the mixture was partitioned between EA and 2 N hydrochloric acid
  2. dry with materialthe combined organic extracts were dried over sodium chloride
  3. customdecanted
  4. customevaporated to dryness
  5. customThe raw material was purified by silica gel chromatography (EA/HEP gradient 0:1 to 4:6)

Sources & evidence

ORD record
ord-9ebdbb0334ea45b786989542c1de9505
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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