Bicarbonate Ion → 1-[(5-Bromo-2-chloro-phenyl)methyl]-2,3-difluoro-4-methoxy-benzene

HRID 1055569ノート

反応式

HRID 1055569 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([F:18])[C:11]=2[F:19])=O)[CH:7]=1.B(F)(F)F.CCOCC.C(OCC)(=O)C.C(=O)(O)[O-]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([F:18])[C:11]=2[F:19])[CH:7]=1

参加物

6

反応物 4

HCID 769Bicarbonate IonHCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 89576925(5-Bromo-2-chloro-phenyl)-(2,3-difluoro-4-methoxy-phenyl)methanone

生成物 1

HCID 866851071-[(5-Bromo-2-chloro-phenyl)methyl]-2,3-difluoro-4-methoxy-benzene収率 25.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (5-bromo-2-chloro-phenyl)-(2,3-difluoro-4-methoxy-phenyl)methanone 21e (5.42 g, 14.9 mmol) in acetonitrile (100 mL) were added triethyl silicane (4.8 mL, 29.87 mmol) at 15° C., followed by boron trifluoride diethyl ether (7.4 mL, 59.74 mmol). The mixture was warmed up to room temperature and stirred for 15 hours. To the reaction mixture was added ethyl acetate (4 mL). The mixture was adjusted with saturated aqueous bicarbonate to pH 7, and then partitioned. The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=20/1 to give the title compound 21f as pale yellow oil (1.34 g, 25.8%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 347.05 [M+H]+; and 1H NMR (400 MHz, CDCl3) δ (ppm): 7.33 (m, 1H), 7.28 (m, 2H), 6.84-6.76 (m, 1H), 6.75-6.62 (m, 1H), 4.05 (s, 2H), 3.91 (s, 3H).

後処理

  1. custompartitioned
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel chromatography
  6. washeluted with PE/EtOAc(v/v)=20/1

出典と根拠

ORDレコード
ord-55bcdf5271da447982560e6e0bcf2973
出典データセット
uspto-grants-2016_07
特許番号
US09394329B2

反応ノート

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