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

HRID 229178Notes

Reaction equation

HRID 229178 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH3:18].[Al+3].[Cl-].[Cl-].[Cl-].O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 68654384(4-Bromo-3-methylphenyl)(4-methoxyphenyl)methanone

Product 1

HCID 68654843(4-Bromo-3-methylphenyl)(4-hydroxyphenyl)methanoneYield 93.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 65 (2.00 g, 6.55 mmol) and AlCl3 (3.50 g, 26.2 mmol) were refluxed in benzene (50 mL) for 3 h and then cooled to RT. Water (100 mL) was cautiously added dropwise, and the mixture was extracted with Et2O (3×100 mL). The combined ethereal extracts were washed with water (200 mL), brine (200 mL), and dried over MgSO4. Concentration afforded 1.78 g (93%) of 66 that was used without further purification. 1H NMR (400 MHz, CDCl3): δ 2.45 (s, 3H), 5.68 (br s, 1H), 6.90 (d, J=8.6 Hz, 2H), 7.40 (dd, J=8.2 Hz, 1.8 Hz, 1H), 7.63 (m, 2H), 7.75 (d, J=8.6 Hz, 2H).

Workup

  1. extractionthe mixture was extracted with Et2O (3×100 mL)
  2. washThe combined ethereal extracts were washed with water (200 mL), brine (200 mL)
  3. dry with materialdried over MgSO4
  4. concentrationConcentration

Sources & evidence

ORD record
ord-bab015ff4b1d4909b68f8f228c5dbc11
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

Loading…