O-Cresol → HCID 68654549, compound

HRID 1716005Notes

Reaction equation

HRID 1716005 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]1([CH3:18])[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:13]2[CH:14]=[CH:15][C:16]([OH:17])=[C:11]([CH3:18])[CH:12]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 335O-CresolHCID 962WaterHCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 68654549HCID 68654549, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzoyl chloride (1.04 g, 4.74 mmol) and o-cresol (0.58 g, 5.33 mmol) in CH2Cl2 (20 mL) was added AlCl3 (0.76 g, 5.72 mmol) portion-wise. The mixture was allowed to warm to RT over 12 h. Water was added, and the mixture was extracted with CH2Cl2. The organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography on silica gel (EtOAc:hexanes) to yield 0.21 g (15%) of compound 32. 1H NMR (400 MHz, DMSO-d6): δ 2.15 (s, 3H), 6.89 (d, J=8.3 Hz, 1H), 7.46 (dd, J=2.2 Hz, 8.4 Hz, 1H), 7.54 (d, J=1.9 Hz, 1H), 7.58 (d, 2H), 7.72 (d, 2H), 10.42 (s, 1H).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organics were dried with MgSO4
  3. concentrationconcentrated
  4. customThe crude material was purified by chromatography on silica gel (EtOAc:hexanes)

Sources & evidence

ORD record
ord-e6c12cd1607e4cf59aebc77c9ba15729
Source dataset
uspto-grants-2010_09
Patent number
US07799828B2

Reaction notes

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