Sodium Carbonate → 5-(4-Fluorophenyl)-6-[4-(methylthio)phenyl]-1,3-benzodioxole

HRID 1598841노트

반응식

HRID 1598841 반응식
Br[C:2]1[C:10](Br)=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.[CH3:22][S:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=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:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:10]([C:27]3[CH:28]=[CH:29][C:24]([S:23][CH3:22])=[CH:25][CH:26]=3)=[CH:9][C:5]3[O:6][CH2:7][O:8][C:4]=3[CH:3]=2)=[CH:15][CH:14]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 2258145,6-Dibromo-1,3-dioxaindaneHCID 2856454-Fluorophenylboronic acidHCID 27339594-(Methylthio)phenylboronic acid

생성물 1

HCID 108308475-(4-Fluorophenyl)-6-[4-(methylthio)phenyl]-1,3-benzodioxole수율 142.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

Under nitrogen, 1 g of Pd(PPh3)4 was added to a stirred solution of 4 g (14.3 mmol) of 5,6-dibromo-1,3-benzodioxole (Lancaster), 2.4 g (17.2 mmol) of 4-fluorophenyl boronic acid, and 2.87 g (17.2 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2) in 70 mL of toluene, 40 mL of ethanol, and 30 mL of 2M Na2CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried over Na2 SO4. Concentration in vacuo gave 6.9 g of 5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]-1,3-benzodioxole 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 was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried over Na2 SO4
  6. concentrationConcentration in vacuo

출처 및 근거

ORD 기록
ord-692ea6792de14155887aaeb3fdd82e1d
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739166

반응 노트

불러오는 중…