Water → Methyl 3-(2-tert-butoxy-2-oxoethoxy)-4-chlorobenzoate

HRID 2421041Notes

Reaction equation

HRID 2421041 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[Cs+].[Cs+].[C:19]([O:23][C:24](=[O:27])[CH2:25]Br)([CH3:22])([CH3:21])[CH3:20].O>CN(C=O)C>[C:19]([O:23][C:24](=[O:27])[CH2:25][O:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[Cl:1])[C:6]([O:8][CH3:9])=[O:7])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 11819787Methyl 4-chloro-3-hydroxybenzoate

Product 1

HCID 67215087Methyl 3-(2-tert-butoxy-2-oxoethoxy)-4-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-chloro-3-hydroxybenzoate [Chem. Pharm. Bull. 1994, 42(11),2365-9] (0.73 g), caesium carbonate (1.27 g) and tert butylbromoacetate (0.58 mL) in DMF (6 mL) were heated and stirred at 60° C. for 3 h. Water was added and the product was extracted into ethyl acetate. The extracts were dried over sodium sulphate, filtered and the solvent was evaporated. The resulting oil was purified by flash chromatography, using 1:10 ethyl acetate/isohexane as eluent, to yield the subtitle compound as a colourless oil (1.25 g).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. dry with materialThe extracts were dried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe resulting oil was purified by flash chromatography

Sources & evidence

ORD record
ord-733c534a2e2448f88aa84aebbe00f5d4
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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