N,N-Dimethylaniline → 3,5-Dibromophenol

HRID 1246658Notes

Reaction equation

HRID 1246658 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[C:10]([O:12]CC2C=CC=CC=2)[CH:9]=[C:8]([Br:20])[CH:7]=1.CN(C)C1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([Br:20])[CH:7]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 147841501-(Benzyloxy)-3,5-dibromobenzene

Product 1

HCID 122803,5-DibromophenolYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium chloride (11.7 g, 87.6 mmol) was added in portions to a solution of 1,3-dibromo-5-benzyloxybenzene (10.0 g, 29.2 mmol; see step (i) above) and N,N-dimethylaniline (35.4 g, 292 mmol) in CH2Cl2 (100 mL) at room temperature under a nitrogen atmosphere. After 30 min, the mixture was partitioned with 1N HCl (300 mL) and EtOAc (5×150 mL). The combined organic extracts were washed with saturated NaHCO3 (150 mL) and brine (150 mL) then, dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with Hex:EtOAc (9:1) afforded the sub-title compound (6.1 g, 82%) as a white solid.

Workup

  1. customthe mixture was partitioned with 1N HCl (300 mL) and EtOAc (5×150 mL)
  2. washThe combined organic extracts were washed with saturated NaHCO3 (150 mL) and brine (150 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1033d0d1ec10452a876ba5e4dfe45c0b
Source dataset
uspto-grants-2006_10
Patent number
US07129233B2

Reaction notes

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