Phosphorus tribromide → 4-Bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester

HRID 2121242Notes

Reaction equation

HRID 2121242 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].[Br-].[Li+].P(Br)(Br)[Br:23]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:23])=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 82050Lithium BromideHCID 113912084-Hydroxymethyl-2-(2-methylphenyl)benzoic acid methyl ester

Product 1

HCID 234362594-Bromomethyl-2-(2-methylphenyl)benzoic acid methyl esterYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-hydroxymethyl-2-(2-methylphenyl)benzoic acid methyl ester prepared in Example 331A (10.85 g, 42.2 mmol) in dry DMF (40 mL) at 0° C. was added successively lithium bromide (4.00 g, 46.6 mmol, 1.1 eq) and phosphorus tribromide (4.18 mL, 44.5 mmol, 1.05 eq) at a rate such that the temperature did not exceed 5° C. On completion of the addition the mixture was warmed to ambient temperature, and quenched by the addition of ice. The resultant solution was partitioned between water and ether; the ethereal solution was dried (Na2SO4), filtered and the solvent removed under reduced pressure to afford the title compound (13 g, 96%) as a colorless oil.

Workup

  1. customdid not exceed 5° C
  2. additionOn completion of the addition the mixture
  3. customquenched by the addition of ice
  4. customThe resultant solution was partitioned between water and ether
  5. dry with materialthe ethereal solution was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7143d064ffb74fa49e62e98654ce7e2e
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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