4-Bromophenol → 3-Methyl-but-2-enoic acid 4-bromo-phenyl ester

HRID 1608934Notes

Reaction equation

HRID 1608934 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:11][C:12]([CH3:17])=[CH:13][C:14](Cl)=[O:15]>C1COCC1>[CH3:11][C:12]([CH3:17])=[CH:13][C:14]([O:10][C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=1)=[O:15]

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 24758Sodium hydrideHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 7337973-Methyl-but-2-enoic acid 4-bromo-phenyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To an ice bath cooled solution of 1.66 g (69.2 mmol) of NaH (60% suspension in mineral oil) in 25 ml of dry THF was added slowly under argon a solution of 10.0 g (57.8 mmol) of 4-bromophenol in 50 ml of dry THF. The mixture was stirred at 0 degrees C. for 30 minutes and then treated with a solution of 6.85 g (6.44 ml, 57.8 mmol) of dimethylacryloyl chloride in 25 ml of dry THF. The cooling bath was then removed and the mixture allowed to warm to room temperature. The organic layer was separated and the aqueous layer was washed with 2×25 ml of ether. The combined organic layers were washed with 2×50 ml of water, brine and dried (MgSO4). The solvent was removed in-vacuo and the residue purified using flash chromatography (SiO2 ; 5% ethyl acetate in hexanes) to give the title compound as a pale yellow oil.

Workup

  1. customThe cooling bath was then removed
  2. temperatureto warm to room temperature
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with 2×25 ml of ether
  5. washThe combined organic layers were washed with 2×50 ml of water, brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in-vacuo
  8. customthe residue purified

Sources & evidence

ORD record
ord-d9e3899926ee4745ae730caf5ff29f10
Source dataset
uspto-grants-1995_03
Patent number
US05399561

Reaction notes

Loading…