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

HRID 30755

반응식

HRID 30755 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-29c629dfd82e403abf56ff372f921911
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423185B2

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