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

HRID 2217111ノート

反応式

HRID 2217111 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 693130294-Benzyloxy-4'-(trifluoromethoxy)biphenyl収率 35.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2f9392ae39e84e32ae39be28ded178ed
出典データセット
uspto-grants-2008_08
特許番号
US07407691B2

反応ノート

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