Benzyl Bromide → Methyl 5-bromo-2,4-dibenzyloxybenzoate

HRID 1643334Notes

Reaction equation

HRID 1643334 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[C:9]([OH:19])=[CH:10][C:11]([OH:18])=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[Br:7][C:8]1[C:9]([O:19][CH2:13][C:12]2[CH:17]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:10][C:11]([O:18][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 44828918Methyl 5-bromo-2,4-dihydroxybenzoate

Product 1

HCID 59317108Methyl 5-bromo-2,4-dibenzyloxybenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.2 92.6 g of potassium carbonate are added to a solution of 80 g of methyl 5-bromo-2,4-dihydroxybenzoate in 1 l of acetonitrile, and 77 ml of benzyl bromide are added dropwise. The mixture is heated for 3 hours and cooled, the solvent is removed, and the residue is subjected to conventional work-up, giving 150 g of methyl 5-bromo-2,4-dibenzyloxybenzoate (crude product).

Workup

  1. additionare added dropwise
  2. temperatureThe mixture is heated for 3 hours
  3. temperaturecooled
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-cb305b13ae1d4f2c9d38c81c8475bdd5
Source dataset
uspto-grants-2012_02
Patent number
US08119795B2

Reaction notes

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