Benzyl Bromide → Methyl 3-(benzyloxy)-4-iodobenzoate

HRID 250841Notes

Reaction equation

HRID 250841 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[I:20])[C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[I:20])[C:13]([O:15][CH3:16])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 57443321Methyl 3-(benzyloxy)-4-iodobenzoateYield 104.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

2.35 mL (19.78 mmol, 1.1 eq) of benzyl bromide are added to a solution of 5.0 g (17.98 mmol, 1 eq) of methyl 3-hydroxy-4-iodobenzoate in 30 ml of methyl ethyl ketone in the presence of 5.0 g (36.18 mmol, 2 eq) of potassium carbonate. The reaction mixture is heated at 60° C. for 5 hours and then hydrolyzed in water and extracted with ethyl acetate. 6.9 g of methyl 3-benzyloxy-4-iodobenzoate are obtained in oil form and are used in the following reaction without further purification.

Workup

  1. extractionhydrolyzed in water and extracted with ethyl acetate

Sources & evidence

ORD record
ord-bc0c9322904546e8a09cd3c1b768dc4a
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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