Hydrogen Bromide → HCID 80147526、化合物

HRID 1963048ノート

反応式

HRID 1963048 の反応式
C[Si](C=[N+]=[N-])(C)C.[CH3:8]CCCCC.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[CH2:22][C:23](Cl)=[O:24].[BrH:26]>O.C(#N)C.C1COCC1>[Br:26][CH2:8][C:23](=[O:24])[CH2:22][C:16]1[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14]

参加物

8

反応物 4

HCID 260Hydrogen BromideHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 217957352-Chloro-6-fluorobenzeneacetyl chloride

生成物 1

HCID 80147526HCID 80147526、化合物収率 76.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a 2 M solution of trimethylsilyl-diazomethane in hexane (6.54 ml, 13.07 mmol) cooled to 0° C. under argon was added dropwise a solution of 2-chloro-6-fluoro-phenylacetyl chloride (1.23 g, 5.94 mmol) in 24 ml of a mixture of THF and ACN (1:1). The mixture was stirred at 0° C. for 5 h. Then 48% aqueous hydrobromic acid (5.91 ml, 52.28 mmol) was added dropwise and the solution was stirred at room temperature overnight. Then 40 ml of water were added. The aqueous phase was extracted twice with EA, and the combined organic phases were washed with water, a saturated solution of sodium hydrogencarbonate and brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0, then 95:5) to give 1.20 g of the title compound as a white powder having a melting point of 47° C.

後処理

  1. stirringthe solution was stirred at room temperature overnight
  2. extractionThe aqueous phase was extracted twice with EA
  3. washthe combined organic phases were washed with water
  4. dry with materiala saturated solution of sodium hydrogencarbonate and brine, dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0

出典と根拠

ORDレコード
ord-1577596bd8a94949ba14809710d59ec3
出典データセット
uspto-grants-2013_04
特許番号
US08415336B2

反応ノート

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