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

HRID 2387874Notes

Reaction equation

HRID 2387874 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.C([O-])([O-])=O.[K+].[K+]>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

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 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 K2CO3 (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-c14ff9b2809f484e90086b0ad46c1d20
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

Loading…