Sodium Carbonate → Tert-butyl 2-methyl-4-(1-phenylvinyl)benzoate

HRID 1501198

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HRID 1501198 반응식
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([CH3:15])[CH:3]=1.[CH:16](B1OC(C)(C)C(C)(C)O1)=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.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>[CH3:15][C:4]1[CH:3]=[C:2]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH2:16])[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2774014trans-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styreneHCID 53432590tert-Butyl 4-bromo-2-methylbenzoate

생성물 1

HCID 89580861Tert-butyl 2-methyl-4-(1-phenylvinyl)benzoate수율 91%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

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온도
90 °C

실험 절차

To a solution of tert-butyl 4-bromo-2-methylbenzoate (2 g, 7 mmol) in dioxane/water (50 mL, 4:1) was added styrylboronic acid pinacol ester (1.64 g, 7 mmol), tetrakis(triphenylphosphine)palladium (0.7 mmol, 0.904 g), sodium carbonate (21 mmol, 2.3 g). The mixture was stirred at 90° C. under nitrogen gas atmosphere for 18 hours. LC-MS showed the start material has been consumed. Then evaporated the solvent and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=30:1) to give tert-butyl 2-methyl-4-(1-phenylvinyl)benzoate (1.8 g, 91%).

후처리

  1. customhas been consumed
  2. customThen evaporated the solvent
  3. custompurified by column chromatography (silica gel, petroleum ether/ethyl acetate=30:1)

출처 및 근거

ORD 기록
ord-6e3fd55ee1614afb8b1c9448a345a5bd
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

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