O-Cresol → HCID 68654549, compound

HRID 229153Notes

Reaction equation

HRID 229153 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, compound

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 0.219 (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-dad473e8a0894a53ac3390c0926eb1ee
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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