1,2-Dimethoxyethane → 4-Benzyloxy-4'-(trifluoromethoxy)biphenyl

HRID 2217111노트

반응식

HRID 2217111 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]([F:29])([F:28])[O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>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.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:22]2[CH:21]=[CH:20][C:19]([O:18][C:17]([F:16])([F:28])[F:29])=[CH:24][CH:23]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 27343864-(Trifluoromethoxy)phenylboronic acid

생성물 1

HCID 693130294-Benzyloxy-4'-(trifluoromethoxy)biphenyl수율 35.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

A reaction mixture comprising 6.7 g of 4-benzyloxybromobenzene, 5.0 g of 4-(trifluoromethoxy)benzeneboronic acid, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 5.1 g of sodium carbonate, 100 ml of ethylene glycol dimethyl ether and 20 ml of pure water was refluxed for 5 hours. The reaction mixture was extracted with toluene, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was purified through silica gel chromatography (elution solvent: heptane/toluene=7/3) and recrystallized from heptane, and 3.0 g of 4-benzyloxy-4′-(trifluoromethoxy)biphenyl was obtained. m.p.: 136-137.2° C.

후처리

  1. extractionThe reaction mixture was extracted with toluene
  2. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  3. customThe solvent was evaporated away
  4. customthe resulting residue was purified through silica gel chromatography (elution solvent: heptane/toluene=7/3)
  5. customrecrystallized from heptane

출처 및 근거

ORD 기록
ord-2f9392ae39e84e32ae39be28ded178ed
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407691B2

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