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

HRID 1927696Notes

Reaction equation

HRID 1927696 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[CH2:20]([O:12][C:5]1[CH:4]=[C:3]([O:13][CH2:7][C:6]2[CH:11]=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:2]([Br:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

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

Conditions

Temperature
80 °C

Procedure

7.86 kg of methyl 5-bromo-2,4-dihydroxybenzoate and 9.65 kg of potassium carbonate are suspended in 100 l of acetonitrile at 0° C. The mixture is subsequently heated to 80° C., and 7575 ml of benzyl bromide are added via a dropping funnel over a period of 40 min. After stirring overnight at 80° C., the mixture is filtered, and the collected filtrate is evaporated in vacuo: 12.95 kg (95%) of methyl 2,4-bisbenzyloxy-5-bromobenzoate (slightly yellow crystals); MW 427.3.

Workup

  1. filtrationthe mixture is filtered
  2. customthe collected filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-8db0890c0f4b4d7bb6ee82b13568d582
Source dataset
uspto-grants-2012_05
Patent number
US08183279B2

Reaction notes

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