Imidazole → Methyl 3-bromo-5-(iodomethyl)-4-methylbenzoate

HRID 337659Notes

Reaction equation

HRID 337659 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.N1C=CN=C1.[Br:27][C:28]1[CH:29]=[C:30]([CH:35]=[C:36]([CH2:39]O)[C:37]=1[CH3:38])[C:31]([O:33][CH3:34])=[O:32]>ClCCl>[Br:27][C:28]1[CH:29]=[C:30]([CH:35]=[C:36]([CH2:39][I:20])[C:37]=1[CH3:38])[C:31]([O:33][CH3:34])=[O:32]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 66896191Methyl 3-bromo-5-(hydroxymethyl)-4-methylbenzoate

Product 1

HCID 66896553Methyl 3-bromo-5-(iodomethyl)-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (0.05 M) solution of triphenylphosphine (1.1 eq) was added iodine (1.1 eq.). The resulting orange-yellow suspension was stirred at RT for 30 min before imidazole (1.2 eq.) and finally methyl 3-bromo-5-(hydroxymethyl)-4-methylbenzoate (1 eq.) from the previous step were added. The now pale yellow solution was stirred at RT for another 30 min. The volatiles were removed in vacuo and the residue was triturated with a 1:1 (v/v) mixture of hexanes and ether. The insolubles were then removed via filtration through a pad of silica gel. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. additionwere added
  2. customThe volatiles were removed in vacuo
  3. customthe residue was triturated with a 1:1 (v/v) mixture of hexanes and ether
  4. customThe insolubles were then removed via filtration through a pad of silica gel

Sources & evidence

ORD record
ord-2abfda4e64324c5b9869a32e5436db68
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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