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

HRID 2100156노트

반응식

HRID 2100156 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9a76a06c142447e5a3d4e58f2dfc7406
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569601B2

반응 노트

불러오는 중…