Dimethylformamide → Ethyl 5-bromo-2-ethoxy-4-methylbenzoate

HRID 1295921Notes

Reaction equation

HRID 1295921 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5](O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13](=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH3:20].CN(C)[CH:24]=[O:25]>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([O:25][CH2:24][CH3:13])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:19][CH3:20])=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2439345-bromo-2-hydroxy-4-methylbenzoic acid

Product 1

HCID 22929763Ethyl 5-bromo-2-ethoxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

After dissolving 5-bromo-2-hydroxy-4-methylbenzoic acid (9.35 g) in dimethylformamide, potassium carbonate (14 g) and ethyl iodide (8 ml) were added in that order and the mixture was stirred at 50° C. for 3 hours. It was then diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to yield ethyl 5-bromo-2-ethoxy-4-methylbenzoate. The product was dissolved in ethanol (100 ml), 5 N sodium hydroxide (20 ml) was added and the mixture was heated to reflux for 30 minutes. After adding 5 N hydrochloric acid (25 ml) for neutralization, extraction was performed with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated to yield the title compound (10.4 g) as a white solid.

Workup

  1. additionwere added in that order
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a77b0601025942b6bf398b731656b7d4
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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