Sodium Iodide → Benzene, 4-bromo-2-[(4,4-difluoro-3-buten-1-yl)oxy]-1-fluoro-

HRID 30593

反応式

HRID 30593 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(C(C)=O)C.ClCCl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:9][CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23])[CH:4]=1

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 183421Phenol, 5-bromo-2-fluoro-HCID 27822404-Bromo-1,1-difluorobut-1-ene

生成物 1

HCID 59790300Benzene, 4-bromo-2-[(4,4-difluoro-3-buten-1-yl)oxy]-1-fluoro-収率 63%

試薬・触媒・溶媒 3

HCID 21218Trioctylmethylammonium chloride触媒HCID 6344Dichloromethane溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A mixture of 2-fluoro-5-bromophenol (2.40 g), potassium carbonate (2.31 m), Aliquat 336 (5 drops), sodium iodide (catalytic) and 4-bromo-1,1-difluoro-1-butene (1.79 mL) in methyl ethyl ketone was placed in a pressure vessel and heated in a 82° oil bath for 15 hours. The reaction mixture was cooled, diluted with dichloromethane, filtered and evaporated in vacuo. The resultant residue was purified by flash chromatography (silica gel, eluant: 2.5% ethyl acetate/hexane to afford 4-bromo-2-(4,4-difluorobut-3-enyloxy)-1-fluorobenzene, 2.23 g (63% yield), identified by NMR analysis.

後処理

  1. customwas placed in a pressure vessel
  2. temperatureheated in a 82° oil bath for 15 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resultant residue was purified by flash chromatography (silica gel, eluant

出典と根拠

ORDレコード
ord-64e03f43ee504125a8fbde98ebe10950
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

関連ノート

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