3-Bromo-4-fluorobenzyl Alcohol → Ethyl 3-(3-bromo-4-fluorophenyl)acrylate

HRID 1476065Notes

Reaction equation

HRID 1476065 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5]O.[CH2:11]([O:13][C:14]([CH:16]=[PH3])=[O:15])[CH3:12]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:16][C:14]([O:13][CH2:11][CH3:12])=[O:15])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 2

HCID 27733513-Bromo-4-fluorobenzyl AlcoholHCID 178473136HCID 178473136, compound

Product 1

HCID 67207802Ethyl 3-(3-bromo-4-fluorophenyl)acrylate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

9.65 g (111 mmol) of manganese dioxide were added to a solution of 6.5 g (31.7 mmol) of 3-bromo-4-fluorobenzyl alcohol and 13.25 g (38 mmol) of ethoxycarbonylmethylenephosphorane in 390 ml of toluene. The reaction mixture was heated at reflux, a further 9.65 g of manganese dioxide were added after 1 h and heating under reflux was continued overnight. After cooling, the mixture was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (mobile phase cylclohexane/ethyl acetate 5:1). This gave 7.05 g (81% of theory) of the target product in the form of an E/Z isomer mixture.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. temperatureheating
  4. temperatureunder reflux
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered through celite
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by flash chromatography on silica gel (mobile phase cylclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-462838c40a2c4dd6a4a34103807a564b
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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