Imidazole → 5-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenyliodomethane

HRID 730175Notes

Reaction equation

HRID 730175 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]=[CH:30][C:31]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([O:44][CH3:45])[C:39]=2[CH3:46])=[C:32]([CH2:34]O)[CH:33]=1>ClCCl>[Br:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([O:44][CH3:45])[C:39]=2[CH3:46])=[C:32]([CH2:34][I:20])[CH:33]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 578344865-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenylmethanol

Product 1

HCID 578344845-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenyliodomethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To polymer-supported triphenylphosphine (9.2 g; ˜27.5 mmol) in dichloromethane (40 mL) was added iodine (6.98 g; 27.5 mmol). The mixture was stirred for 30 minutes and then imidazole (1.87 g; 27.5 mmol) was added to the mixture. After stirring for 15 minutes a solution of 5-bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenylmethanol 8 (4.19 g; 12.5 mmol) in dichloromethane (100 mL) was added. The mixture was heated at reflux for 2 hours, cooled to room temperature and filtered. The filtrate was washed sequentially with sodium thiosulfate solution, water, and brine, dried over MgSO4, and concentrated to dryness at ambient temperature under high vacuum to give compound 9 as a yellow oil, 5.56 g.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 2 hours
  4. filtrationfiltered
  5. washThe filtrate was washed sequentially with sodium thiosulfate solution, water, and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness at ambient temperature under high vacuum

Sources & evidence

ORD record
ord-82635c587c6a4bcb86638cc904dc7a0e
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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