Phosphorus tribromide → Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

HRID 53436Notes

Reaction equation

HRID 53436 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.P(Br)(Br)[Br:20].C(=O)([O-])O.[Na+]>N1C=CC=CC=1.CCCCCC>[Br:20][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 15380881Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateYield 100.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent

Procedure

10.0 g (41 mmol) of methyl 2-(4'-hydroxymethylphenyl)benzoate was dissolved in 7.9 g of pyridine and n-hexane (100 ml). 8.3 g (31 mmol) of phosphorus tribromide was dropwise added thereto under cooling with ice, followed by stirring for 2 hours as such. The reaction liquid was added to an aqueous solution of sodium hydrogencarbonate, followed by the extraction with n-hexane. The organic phase was washed with water, dried and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 9.5 g of the title compound (yield 75%).

Workup

  1. temperatureunder cooling with ice
  2. customThe reaction liquid
  3. extractionfollowed by the extraction with n-hexane
  4. washThe organic phase was washed with water
  5. customdried
  6. concentrationsubjected to vacuum concentration
  7. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-809eab52bd254a1ebf3d41a7e05b4e05
Source dataset
uspto-grants-1997_04
Patent number
US05618969

Reaction notes

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