Sodium Carbonate → HCID 59456349、化合物

HRID 1873409

反応式

HRID 1873409 の反応式
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18](B(O)O)=[C:17]([F:24])[C:16]=2[F:25])[CH2:11][CH2:10]1)[CH3:8].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:7]([CH:9]1[CH2:10][CH2:11][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([C:2]3[Se:3][CH:4]=[CH:5][CH:6]=3)=[C:17]([F:24])[C:16]=2[F:25])[CH2:13][CH2:14]1)[CH3:8]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 1370132-BromoselenopheneHCID 59456333HCID 59456333、化合物

生成物 1

HCID 59456349HCID 59456349、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21863594Toluene ethanol溶媒

実験手順

A mixture of 8.9 g (42.4 mmol) of 2-bromoselenophene, 16.0 g (59.7 mmol) of 4-(4-ethylcyclohexyl)-2,3-difluorophenylboronic acid, 3.93 g (3.40 mmol) of tetrakis(triphenylphosphine)palladium(0) and 125 ml of 2 N sodium carbonate soln. in 600 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with sat. sodium chloride soln., and the solution is dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). The further purification is carried out by recrystallisation from n-heptane:EtOH=1:1 and IPA. 2-[4-(4-Ethylcyclohexyl)-2,3-difluorophenyl]selenophene is obtained as a pale-yellowish solid.

後処理

  1. temperatureunder reflux for 20 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted with toluene
  5. washThe combined organic phases are washed with sat. sodium chloride soln
  6. custom, and the solution is dried
  7. concentrationThe solution is concentrated to dryness
  8. customthe residue is purified by column chromatography (SiO2, toluene)
  9. customThe further purification
  10. customis carried out by recrystallisation from n-heptane

出典と根拠

ORDレコード
ord-9141115f49904b5e9db82f30946f0890
出典データセット
uspto-grants-2012_11
特許番号
US08304036B2

関連ノート

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