3-Methoxytoluene → (4-Bromophenyl)[2-methyl-4-(methyloxy)phenyl]methanone

HRID 229148

Reaction equation

HRID 229148 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:13]=[C:14]([O:18][CH3:19])[CH:15]=[CH:16][CH:17]=1.[Al+3].[Cl-].[Cl-].[Cl-]>O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:17]2[CH:16]=[CH:15][C:14]([O:18][CH3:19])=[CH:13][C:12]=2[CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 75303-MethoxytolueneHCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11023132(4-Bromophenyl)[2-methyl-4-(methyloxy)phenyl]methanoneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-bromobenzoyl chloride (1.12 g, 5.12 mmol) and 3-methyl anisole (1.95 mL, 15.47 mmol) at 0° C. was added AlCl3 (0.83 g, 6.20 mmol). The mixture was allowed to warm to RT over 12 h with stirring. Water was added slowly, 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 1.14 g (73%) of compound 27. 1H NMR (400 MHz, CDCl3): δ 2.41 (s, 3H), 3.86 (s, 3H), 6.74 (dd, J=2.5 Hz, 8.6 Hz, 1H), 6.82 (d, J=2.6 Hz, 1H), 7.31 (d, J=8.6 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.62 (d, J=8.5 Hz, 2H).

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-c25237681b384baa81e76366647fb27b
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Linked notes

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