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

HRID 2100156ノート

反応式

HRID 2100156 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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 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, 2 H), 7.43 (d, J=8.2 Hz, 1 H), 7.61 (d, J=8.2 Hz, 1 H), 7.69 (d, J=8.7 Hz, 2 H), 7.89 (t, J=7.1 Hz, 1H), 10.54 (s, 1 H).

後処理

  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 washed with brine (200 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-9a76a06c142447e5a3d4e58f2dfc7406
出典データセット
uspto-grants-2009_08
特許番号
US07569601B2

反応ノート

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