Hydrochloric Acid → 1-Tert-butyl-3-iodo-2-methoxy-5-(1-phenylvinyl)benzene

HRID 403683노트

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HRID 403683 반응식
[C:1]([C:5]1[CH:10]=[C:9](I)[CH:8]=[C:7]([I:12])[C:6]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[C:15]1([C:21](B(O)O)=[CH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+].Cl>C(COC)OC.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>[C:1]([C:5]1[CH:10]=[C:9]([C:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH2:22])[CH:8]=[C:7]([I:12])[C:6]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5003684(1-Phenylvinyl)boronic acidHCID 574194401-(Tert-butyl)-3,5-diiodo-2-methoxybenzene

생성물 1

HCID 667000441-Tert-butyl-3-iodo-2-methoxy-5-(1-phenylvinyl)benzene

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

A solution of 1-tert-butyl-3,5-diiodo-2-methoxybenzene (4.94 g, 11.87 mmol) in dimethoxyethane (50 mL) and water (30 mL) was treated with 1-phenylvinylboronic acid (2.283 g, 15.43 mmol), tetrakis(triphenylphosphine)palladium(0) (0.686 g, 0.593 mmol) and sodium bicarbonate (2.492 g, 29.7 mmol) followed by heating at 100° C. for 3 hours. 1 N HCl was added and the mixture was extracted with ethyl acetate, then dried (Na2SO4), filtered and concentrated in vacuo to give crude product which was purified by silica gel flash chromatography eluting with 50:1 hexanes/ethyl acetate to give the title compound.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give crude product which
  6. customwas purified by silica gel flash chromatography
  7. washeluting with 50:1 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-26cb4fe3a52747f381c4dea48aa82ddc
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748443B2

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