Water → (4-Bromo-3-methylphenyl)(4-methoxyphenyl)methanone

HRID 229177Notes

Reaction equation

HRID 229177 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]=1[CH3:15].O.[C:17]1([O:23][CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:20]2[CH:21]=[CH:22][C:17]([O:23][CH3:24])=[CH:18][CH:19]=2)=[O:11])=[CH:8][C:7]=1[CH3:15]

Participants

5

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 70215344-Bromo-3-methylbenzoyl chloride

Product 1

HCID 68654384(4-Bromo-3-methylphenyl)(4-methoxyphenyl)methanoneYield 93%

Procedure

AlCl3 (3.63 g, 27.2 mmol) was added portionwise to 4-bromo-3-methylbenzoyl chloride (5.30 g, 22.7 mmol) dissolved in anisole (7 mL) at 0° C. The reaction mixture was warmed to RT, stirred for 1 h, and then cooled to 0° C. Water (200 mL) was cautiously added dropwise, and the mixture was extracted with ether (3×100 mL). The combined ethereal extracts were washed with water (250 mL), brine (250 mL), and dried over MgSO4. Concentration followed by flash chromatography (20:1 to 5:1 hexanes:EtOAc) afforded 6.42 g (93%) of 65 as a white solid. 1H NMR (400 MHz, CDCl3): δ 2.45 (s, 3H), 3.88 (s, 3H), 6.96 (d, J=8.8 Hz, 2H), 7.40 (d, J=8.1 Hz, 1H), 7.62 (m, 2H), 7.79 (d, J=8.8 Hz, 2H).

Workup

  1. temperaturecooled to 0° C
  2. extractionthe mixture was extracted with ether (3×100 mL)
  3. washThe combined ethereal extracts were washed with water (250 mL), brine (250 mL)
  4. dry with materialdried over MgSO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-9841834aeb394dc0b9ab3706cd720713
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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