Benzyl Bromide → Benzyl 3,5-bis(benzyloxy)-4-bromobenzoate

HRID 1643664Notes

Reaction equation

HRID 1643664 reaction equation
[Br:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:12].C([O-])([O-])=O.[K+].[K+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CN(C=O)C>[CH2:25]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([O:11][CH2:25][C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)[C:2]([Br:1])=[C:3]([O:12][CH2:6][C:5]2[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=2)[CH:4]=1)[C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 860234-Bromo-3,5-dihydroxybenzoic acid

Product 1

HCID 10051813Benzyl 3,5-bis(benzyloxy)-4-bromobenzoateYield 59.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromo-3,5-dihydroxy-benzoic acid (350 g, 1.5 mol) in dry DMF (2 L) were added K2CO3 (725 g, 5.25 mL) and BnBr (769 g, 4.5 mol) in one portion. The mixture was stirred at room temperature for 2 days and then filtered. The filter cake was washed with CH2Cl2. The combined filtrates were concentrated to give the title compound (225 g, 40% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.22-7.52 (m, 17H), 5.38(s, 2H), 5.21 (s, 4H).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with CH2Cl2
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-6835b46d76cb46e49b60e3ce76b6c4df
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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