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Ethanol → Methanesulfonic acid 6-benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yl ester

HRID 1513864
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HRID 1513864 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:14](Br)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:14]([C:29]1[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=1)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86626526Methanesulfonic acid 6-benzyloxy-2-bromo-naphthalen-1-yl ester

생성물 1

HCID 86626527Methanesulfonic acid 6-benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yl ester수율 98%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 1140Toluene용매

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온도
100 °C

실험 절차

Combine methanesulfonic acid 6-benzyloxy-2-bromo-naphthalen-1-yl ester (10.0 g, 24.4 mmol), 4-fluorophenylboronic acid (10.2 g, 729 mmol), sodium carbonate (7.8 g, 73.6 mmol) and tetrakistriphenylphosphine palladium (2.8 g, 2.4 mmol) in a mixture of toluene (300 mL), ethanol (60 mL) and water (40 mL). Heat the mixture at 100° C. for 12 hours. Cool and filter the suspension through a pad of celite. Evaporate the solvent in vacuo. Wash the residue with sodium bicarbonate solution and brine. Dry with magnesium sulfate and concentrate in vacuo. Purify the residue over silica gel, eluting the material with a step gradient of methanol/dichloromethane (0 to 10%), to obtain 10.1 g (98%) of methanesulfonic acid 6-benzyloxy-2-(4-fluoro-phenyl)-naphthalen-1-yl ester.

후처리

  1. temperatureCool
  2. filtrationfilter the suspension through a pad of celite
  3. customEvaporate the solvent in vacuo
  4. washWash the residue with sodium bicarbonate solution and brine
  5. dry with materialDry with magnesium sulfate
  6. concentrationconcentrate in vacuo
  7. customPurify the residue over silica gel
  8. washeluting the material with a step gradient of methanol/dichloromethane (0 to 10%)

출처 및 근거

ORD 기록
ord-cc2710fd49994a50b919740fd671da6a
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217032B2

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