Hydrochloric Acid → (4-Bromo-3-fluorophenyl)(4-hydroxyphenyl)methanone

HRID 229257Notes

Reaction equation

HRID 229257 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[F:18].[Al+3].[Cl-].[Cl-].[Cl-].Cl.CCOC(C)=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[F:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 247227974-Bromo-3-fluoro-4'-methoxybenzophenone

Product 1

HCID 68654588(4-Bromo-3-fluorophenyl)(4-hydroxyphenyl)methanoneYield 112.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of (4-bromo-3-fluorophenyl)[4-(methyloxy)phenyl]methanone (185) (3.20 g, 10.4 mmol) in benzene (80 mL) was slowly added AlCl3 (5.91 g, 44.2 moL, 4.3 eq) via a powder addition funnel under a nitrogen atmosphere at room temperature. The stirred reaction mixture was heated at reflux for 3 h under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature and then poured onto a mixture of 1 N HCl (150 mL) and ice (300 g). The quenched reaction mixture was transferred to a separatory funnel and EtOAc (200 mL) added. The organic phase was separated and the aqueous phase was extracted with EtOAc. The organic phase was washed with brine (200 mL), dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to give 3.44 g of a brown solid. Crystallization from toluene yielded 2.68 g (88%) of the title compound 186 as a brown crystalline solid. 1H NMR (400 MHz, DMSO-d6): δ 6.91 (d, J=8.7 Hz, 2H), 7.43 (d, J=8.2 Hz, 1H), 7.61 (d, J=8.2 Hz, 1H), 7.69 (d, J=8.7 Hz, 2H), 7.89 (t, J=7.1 Hz, 1H), 10.54 (s, 1H).

Workup

  1. additionvia a powder addition funnel under a nitrogen atmosphere at room temperature
  2. customThe stirred reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for 3 h under a nitrogen atmosphere
  5. customThe quenched reaction mixture
  6. customwas transferred to a separatory funnel
  7. customThe organic phase was separated
  8. extractionthe aqueous phase was extracted with EtOAc
  9. washThe organic phase was washed with brine (200 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0dfd44ee808549608a1a96d93494293e
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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