Methyl 3-bromo-5-formylbenzoate → Methyl 3-bromo-5-vinylbenzoate

HRID 1845308Notes

Reaction equation

HRID 1845308 reaction equation
[CH2:1]([Li])CCC.[Br:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([CH:17]=O)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([CH:17]=[CH2:1])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 11436457Methyl 3-bromo-5-formylbenzoateHCID 178418339Butyllithium

Product 1

HCID 58188041Methyl 3-bromo-5-vinylbenzoate

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of methyltriphenylphosphonium bromide (350 mg, 0.97 mmol) in THF (3 mL) at −78° C. under nitrogen was added dropwise 2.5 M of n-butyllithium in tetrahydrofuran (0.31 mL, 0.78 mmol). The mixture was gradually warmed until a yellow color persisted. The mixture was cooled to 0° C. and a solution of methyl 3-bromo-5-formylbenzoate (157 mg, 0.65 mmol) in THF (2 mL) was added dropwise. After being stirred for 20 min at 0° C., the mixture was quenched with saturated aq. NH4Cl and extracted with EtOAc. The organic layer was separated and washed with brine, dried, and concentrated. The residue was purified by flash column to afford the title compound.

Workup

  1. temperatureThe mixture was gradually warmed until a yellow color
  2. customthe mixture was quenched with saturated aq. NH4Cl
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-86c45a0e9602481894e034d3a0e12f67
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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