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

HRID 530667ノート

反応式

HRID 530667 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47e6908f42bc48c199cb8c9e01e3afb7
出典データセット
uspto-grants-2016_05
特許番号
US09353091B2

反応ノート

読み込み中…