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

HRID 250868Notes

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

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 of potassium carbonate. The reaction medium is heated at 60° C. for 5 hours and then hydrolyzed with water and extracted with ethyl acetate. The organic phases are combined and the solvents are evaporated off. 6.9 g of methyl 3-benzyloxy-4-iodobenzoate in oil form are used in the following reaction without further purification.

Workup

extractionhydrolyzed with water and extracted with ethyl acetate
customthe solvents are evaporated off
custom6.9 g of methyl 3-benzyloxy-4-iodobenzoate in oil form are used in the following reaction without further purification

Sources & evidence

ORD record: ord-0263040c308a41218ae5c27f037e12da
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863332B2

Reaction notes

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