Sodium Carbonate → 1,2-Difluoro-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]benzene

HRID 1839932ノート

反応式

HRID 1839932 の反応式
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1Br.[CH3:11][S:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=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>[F:8][C:6]1[CH:7]=[C:2]([C:16]2[CH:17]=[CH:18][C:13]([S:12][CH3:11])=[CH:14][CH:15]=2)[C:3]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)=[CH:4][C:5]=1[F:9]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 949491,2-Dibromo-4,5-difluorobenzeneHCID 2856454-Fluorophenylboronic acidHCID 27339594-(Methylthio)phenylboronic acid

生成物 1

HCID 234513441,2-Difluoro-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]benzene

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

Under nitrogen, 3 g (2.6 mmol) of Pd(PPh3)4 was added to a stirred solution of 5.0 g (18 mmol) of 1,2-dibromo-4,5-difluorobenzene (Aldrich), 4.2 g (25 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2), and 3.1 g (22 mmol) of 4-fluorophenylboronic acid in 100 mL of toluene, 100 mL of ethanol, and 100 mL of 2M Na2CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo and the residue dissolved in ethyl acetate. The resulting solution was washed with water and dried over MgSO4. Purification by silica gel chromatography gave 1,2-difluoro-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]benzene as a semi-solid which was used without further purification.

後処理

  1. temperatureat reflux overnight
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe resulting solution was washed with water
  5. dry with materialdried over MgSO4
  6. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-5e8aee7342874cc4a2ac63bb5c51e683
出典データセット
uspto-grants-2004_01
特許番号
US06677488B2

反応ノート

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