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Sodium Carbonate → 2-(4'-Ethyl-2,3-difluorobiphenyl-4-yl)selenophene

HRID 1873434
ノート
印刷プレビュー

反応式

HRID 1873434 の反応式
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[C:13]([F:14])=[C:12](B(O)O)[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=1.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>[CH2:24]([C:21]1[CH:22]=[CH:23][C:18]([C:9]2[CH:10]=[CH:11][C:12]([C:2]3[Se:3][CH:4]=[CH:5][CH:6]=3)=[C:13]([F:14])[C:8]=2[F:7])=[CH:19][CH:20]=1)[CH3:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 1370132-BromoselenopheneHCID 184694332,3-Difluoro-4'-ethylbiphenyl-4-ylboronic acid

生成物 1

HCID 594562952-(4'-Ethyl-2,3-difluorobiphenyl-4-yl)selenophene

試薬・触媒・溶媒 2

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

実験手順

A mixture of 56.0 g (0.27 mol) of 2-bromoselenophene, 70.0 g (0.27 mol) of 2,3-difluoro-4′-ethylbiphenyl-4-ylboronic acid, 22.0 g (19.0 mmol) of tetrakis(triphenylphosphine)palladium(0) and 800 ml of 2 N sodium carbonate soln. in 2.5 l of toluene/ethanol (1:1) is heated at 90° C. for 17 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with water, 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 ethanol and n-heptane. 2-(4′-Ethyl-2,3-difluorobiphenyl-4-yl)-selenophene is obtained as a yellowish solid.

後処理

  1. temperatureAfter cooling
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted with toluene
  4. washThe combined organic phases are washed with water
  5. customthe solution is dried
  6. concentrationThe solution is concentrated to dryness
  7. customthe residue is purified by column chromatography (SiO2, toluene)
  8. customThe further purification
  9. customis carried out by recrystallisation from ethanol and n-heptane

出典と根拠

ORDレコード
ord-8454be194d104d5eb45a02209f4523d5
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08304036B2

反応ノート

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