Benzyl Bromide → Methyl 2-(benzyloxy)-4-iodobenzoate

HRID 1617222Notes

Reaction equation

HRID 1617222 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 66990993Methyl 2-(benzyloxy)-4-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-hydroxy-4-iodobenzoate (22.8 g), benzyl bromide (10.3 ml) and K2 CO3 (22.67 g) in DMF (200 ml) was stirred at rt for 72 h. The mixture was partitioned between diethyl ether and water, the organics separated washed with water, dried and evaporated under reduced pressure to give a white solid, 29.5 g.

Workup

  1. customThe mixture was partitioned between diethyl ether and water
  2. customthe organics separated
  3. washwashed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customto give a white solid, 29.5 g

Sources & evidence

ORD record
ord-5791fd96ae5941ec9d862054d2e44276
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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