Dimethylformamide → Methyl (3-bromo-4-cyclohexylmethyloxyphenyl)propionate

HRID 2378526Notes

Reaction equation

HRID 2378526 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10]C(OC)=O)[CH:5]=[CH:6][C:7]=1[OH:8].[C:15](=[O:18])([O-])[O-:16].[K+].[K+].Br[CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[CH3:29]N(C=O)C>>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:10])[C:15]([O:16][CH3:29])=[O:18])[CH:5]=[CH:6][C:7]=1[O:8][CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 22558720Methyl 3-(3-bromo-4-hydroxyphenyl)propanoate

Product 1

HCID 86614976Methyl (3-bromo-4-cyclohexylmethyloxyphenyl)propionate

Procedure

A solution of Intermediate 5 (1.29 g) in DMF (25 ml) was added with potassium carbonate (0.86 g) and bromomethylcyclohexane (1.05 ml, TCI), stirred under argon atmosphere at room temperature for 2 hours, then warmed to 60° C., and stirred for 17 hours. The reaction mixture was poured into ice water, and extracted with isopropyl ether (200 ml). The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:isopropyl ether=9:1) to obtain the title compound (Compound No. A-2, 1.45 g).

Workup

  1. temperaturewarmed to 60° C.
  2. stirringstirred for 17 hours
  3. extractionextracted with isopropyl ether (200 ml)
  4. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography (hexane:isopropyl ether=9:1)

Sources & evidence

ORD record
ord-46956679c45045788f258d3b0e5b951e
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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