Hydrochloric Acid → 4-Bromo-3-fluoro-4'-methoxybenzophenone

HRID 229256ノート

反応式

HRID 229256 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[F:11].[C:12]1([O:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:15]2[CH:16]=[CH:17][C:12]([O:18][CH3:19])=[CH:13][CH:14]=2)=[O:7])=[CH:4][C:3]=1[F:11]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 226268914-Bromo-3-fluorobenzoyl chloride

生成物 1

HCID 247227974-Bromo-3-fluoro-4'-methoxybenzophenone収率 83.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-5 °C

実験手順

To a stirred solution of 4-bromo-3-fluorobenzoyl chloride (3.00 g, 12.6 mmol) and anisole (1.65 mL, 1.65 g, 15.2 mmol, 1.20 eq) in DCM (30 mL) at −5° C. was added, portion-wise, over 5 minutes, AlCl3 (2.54 g, 19.0 mmol, 1.50 eq) as a powder. The reaction was stirred at −5° C. for 2 h. The reaction was poured onto a mixture of 1 N HCl (100 mL) and ice (200 g) and stirred for 1 h. The DCM layer was washed with saturated aq. NaHCO3 (100 mL) and brine (100 mL) then dried (MgSO4) and concentrated. The resulting white solid was triturated with ˜100 mL hexanes, filtered and air-dried overnight to afford 3.26 g (83%) of compound 185. 1H NMR (400 MHz, DMSO-d6): δ 3.87 (s, 3H), 7.11 (d, J=8.9 Hz, 2H), 7.45 (d, J=8.9 Hz, 1H), 7.64 (d, J=8.9 Hz, 1H), 7.78 (d, J=8.9 Hz, 2H), 7.91 (t, J=7.1 Hz, 1H).

後処理

  1. stirringstirred for 1 h
  2. washThe DCM layer was washed with saturated aq. NaHCO3 (100 mL) and brine (100 mL)
  3. dry with materialthen dried (MgSO4)
  4. concentrationconcentrated
  5. customThe resulting white solid was triturated with ˜100 mL hexanes
  6. filtrationfiltered
  7. customair-dried overnight

出典と根拠

ORDレコード
ord-87553e4513324219822041c7498da82e
出典データセット
uspto-grants-2009_07
特許番号
US07560589B2

反応ノート

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