4-Methoxyphenol → 2,6-Dibromo-4-methoxyphenol

HRID 1179461Notes

Reaction equation

HRID 1179461 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Br-:10].[Br-:11].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl.CO>[Br:10][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([Br:11])[C:6]=1[OH:9]

Participants

5

Reactant 2

HCID 90154-MethoxyphenolHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 137237142,6-Dibromo-4-methoxyphenolYield 101.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 4-methoxyphenol (10.00 g, 80.6 mmol) in CH2Cl2 (70 mL), add a stirred solution of benzyltrimethylammonium tribromide (69.10 g, 177.2 mmol) in CH2Cl2 (500 mL) and MeOH (200 mL). Stir the reaction for 12 hours and remove the solvent in vacuo. Add methyl tert-butyl ether (MTBE) (600 mL) and collect the precipitate (benzyltrimethylammonium bromide) by filtration and wash with MTBE (200 mL). Filter the organics through Celite® and concentrate to provide the subtitled product (23.0 g, >95%) as an orange solid that may be used without purification. 1H NMR (DMSO-d6) δ 3.69 (s, 3H), 7.14 (s, 2H), 9.32 (s, 1H).

Workup

  1. customthe reaction for 12 hours
  2. customremove the solvent in vacuo
  3. customAdd methyl tert-butyl ether (MTBE) (600 mL) and collect the precipitate (benzyltrimethylammonium bromide)
  4. filtrationby filtration
  5. washwash with MTBE (200 mL)
  6. filtrationFilter the organics through Celite®
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-f639ecf043794f87a27567be0a49fe8f
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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