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

HRID 1839932노트

반응식

HRID 1839932 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5e8aee7342874cc4a2ac63bb5c51e683
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677488B2

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