Cesium fluoride → 4'-(2-Hydroxyethoxy)-3',5'-dimethylbiphenyl-4-carboxylic acid

HRID 30755

反応式

HRID 30755 の反応式
Br[C:2]1[CH:11]=[C:10]([CH3:12])[C:5]([O:6][CH2:7][CH2:8][OH:9])=[C:4]([CH3:13])[CH:3]=1.[C:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([OH:16])=[O:15].[F-].[Cs+].O1CCOCC1>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.C(OCC)(=O)C.O.C(O)C>[OH:9][CH2:8][CH2:7][O:6][C:5]1[C:10]([CH3:12])=[CH:11][C:2]([C:20]2[CH:21]=[CH:22][C:17]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=2)=[CH:3][C:4]=1[CH3:13]

参加物

9

反応物 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 3121834-Carboxyphenylboronic AcidHCID 537074432-(4-Bromo-2,6-dimethylphenoxy)ethanol

生成物 1

HCID 230907314'-(2-Hydroxyethoxy)-3',5'-dimethylbiphenyl-4-carboxylic acid収率 38.2%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-(4-bromo-2,6-dimethylphenoxy)ethanol (0.65 g), 4-carboxyphenylboronic acid (0.87 g), tetrakis(triphenylphosphine)palladium(0) (0.15 g), cesium fluoride (2.40 g), 1,4-dioxane (7.5 mL), ethanol (2.5 mL) and water (1.5 mL) was stirred at 90° C. overnight under an atmosphere of argon. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/1-2/1) to afford the title compound (0.29 g).

後処理

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/1-2/1)

出典と根拠

ORDレコード
ord-29c629dfd82e403abf56ff372f921911
出典データセット
uspto-grants-2008_09
特許番号
US07423185B2

関連ノート

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