Water → (4-Bromophenyl)(3-fluoro-4-hydroxyphenyl)methanone

HRID 229192Notes

Reaction equation

HRID 229192 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)=[C:12]([F:18])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([F:18])[CH:11]=2)=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27569834-Bromo-3'-fluoro-4'-methoxybenzophenoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18434174(4-Bromophenyl)(3-fluoro-4-hydroxyphenyl)methanoneYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 81 (1.28 g, 4.34 mmol) and AlCl3 (3.50 g, 26.2 mmol) were refluxed in benzene (50 mL) for 3 h and cooled to RT. Water (100 mL) was cautiously added dropwise, and the mixture was extracted with ether (3×100 mL). The combined ethereal extracts were washed with water (200 mL), brine (200 mL), and dried over MgSO4. Concentration afforded 1.19 g (98%) of 82 that was used without further purification. 1H NMR (400 MHz, CDCl3): δ 5.80 (br s, 1H), 7.09 (t, J=8.4 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.61-7.64 (m, 5H).

Workup

  1. extractionthe mixture was extracted with ether (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-e416f34e3dd148b9b7bcfe36878a0651
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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