Sodium Carbonate → 3-Bromo-2-phenylthiophene

HRID 234353

反応式

HRID 234353 の反応式
C([O-])([O-])=O.[Na+].[Na+].[C:7]1(OB(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:18]1[S:19][CH:20]=[CH:21][C:22]=1[Br:23]>C(O)C.C1C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:23][C:22]1[CH:21]=[CH:20][S:19][C:18]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 765902,3-DibromothiopheneHCID 78412Phenyl dihydrogen orthoborate

生成物 1

HCID 114818273-Bromo-2-phenylthiophene収率 47%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 241Benzene溶媒HCID 702Ethanol溶媒

実験手順

Tetrakis (triphenylphosphine) palladium (400 mg), Na2CO3 (4M, 80 ml, 320 mmol) and phenylboric acid (3.81 g, 30.3 mmol) as a solution in ethanol (80 ml) were sequentially added to a solution of 2,3-dibromothiophene (7.33 g, 30.3 mmol) in benzene (100 ml). The mixture was heated at reflux for 12 hours. The aqueous layer of the crude mixture was removed and the organic layer was diluted with Et2O (200 ml), washed with 1N NaOH (2×150 ml) and was dried (MgSO2), filtered and the solvent was evaporated. The residue was chromatographed using hexane as the eluent to give 3-bromo-2-phenylthiophene as a clear oil (3.31 g, 47% yield).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 hours
  3. customThe aqueous layer of the crude mixture was removed
  4. additionthe organic layer was diluted with Et2O (200 ml)
  5. washwashed with 1N NaOH (2×150 ml)
  6. dry with materialwas dried (MgSO2)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was chromatographed

出典と根拠

ORDレコード
ord-46457e50f43b41188f183cbcfbc93019
出典データセット
uspto-grants-1997_01
特許番号
US05594021

関連ノート

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