Water → HCID 86056548, compound

HRID 2220415Notes

Reaction equation

HRID 2220415 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:26][CH3:27].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:26][CH3:27])=[O:10])=[C:4]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69103239HCID 69103239, compound

Product 1

HCID 86056548HCID 86056548, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-bromo-2-cyclohexyloxyphenyl)acetic acid (1.33 g) in N,N-dimethylformamide (13 ml) were added potassium carbonate (0.88 g) and iodoethane (1.33 g) at room temperature under nitrogen, and the mixture was stirred at the same temperature for 2.5 days. The resulting mixture was poured into water and the aqueous layer was extracted with a mixture of hexane and ethyl acetate (1:1). The organic layer was washed successively with water (twice) and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/toluene=1:1 to 1:2) to give ethyl (4-bromo-2-cyclohexyloxyphenyl)acetate (1.24 g).

Workup

  1. extractionthe aqueous layer was extracted with a mixture of hexane and ethyl acetate (1:1)
  2. washThe organic layer was washed successively with water (twice) and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/toluene=1:1 to 1:2)

Sources & evidence

ORD record
ord-50b5a69ae48c494f9cc06f8a00272ce2
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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