Water → 4-Bromophenyl acrylate

HRID 883184Notes

Reaction equation

HRID 883184 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[C:11](Cl)(=[O:14])[CH:12]=[CH2:13].O>O1CCCC1>[C:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:14])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 13140Acryloyl chlorideHCID 24758Sodium hydride

Product 1

HCID 137742174-Bromophenyl acrylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromophenol (15.1 g, 87.3 mmol) in tetrahydrofuran (170 mL) was added 60% sodium hydride (3.68 g, 91.6 mmol) under ice-cooling and the mixture was stirred for 15 min. A solution of acryloyl chloride (8.3 g, 91.6 mmol) in tetrahydrofuran (50 mL) was added, and the mixture was stirred for 15 min under ice-cooling. Water was added, and the solvent was evaporated under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (18.1 g, yield 100%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 min under ice-
  3. temperaturecooling
  4. customthe solvent was evaporated under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

Sources & evidence

ORD record
ord-d95078f0389f48b59f93a597f4068f6c
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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