N,N-Dimethylaniline → 3,5-Dibromophenol

HRID 1990742Notes

Reaction equation

HRID 1990742 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-e07baa03baeb4fd48c1b2fd814c3d415
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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