Phenylboronic Acid → 3-Chloro-4-phenyl-1,2,5-thiadiazole

HRID 1167988

反応式

HRID 1167988 の反応式
Br[C:2]1[C:6]([Cl:7])=[N:5][S:4][N:3]=1.[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F-].[K+]>C1(C)C=CC=CC=1.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>[Cl:7][C:6]1[C:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:3][S:4][N:5]=1

参加物

6

反応物 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 101251343-Bromo-4-chloro-1,2,5-thiadiazole

生成物 1

HCID 27640443-Chloro-4-phenyl-1,2,5-thiadiazole収率 95%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

To a mixture of 3-bromo-4-chloro-1,2,5-thiadiazole (0.2 g, 1 mmol), phenylboronic acid (0.135 g, 1.1 mol) in toluene (5 ml) is added a 1M aqueous solution of KF (3 cc, 3 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.055 g, 0.05 mmol, 5%mol) and the biphasic mixture is refluxed with vigorous stirring for 26 hours. The organic layer is decanted off and the aqueous layer is extracted with toluene (2×10 ml). After drying over magnesium sulfate and concentration under vacuum, the oily material is purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (99/1) to afford 0.18 g (95%) of 3-chloro-4-phenyl-1,2,5-thiadiazole as a colorless oil, which crystallizes on standing (melting point 33° C.).

後処理

  1. temperaturethe biphasic mixture is refluxed
  2. customThe organic layer is decanted off
  3. extractionthe aqueous layer is extracted with toluene (2×10 ml)
  4. dry with materialAfter drying over magnesium sulfate and concentration under vacuum
  5. customthe oily material is purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (99/1)

出典と根拠

ORDレコード
ord-e2afbbc0167d4e4cb6251b72d214d0f3
出典データセット
uspto-grants-2003_09
特許番号
US06620940B1

関連ノート

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