Dichloromethane → 2-Methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline

HRID 1700116

反応式

HRID 1700116 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[C:5](Br)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1B(O)O.C(Cl)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>[CH3:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[C:5]([C:16]3[C:17]([CH3:22])=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=3[CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

7

反応物 3

HCID 6344DichloromethaneHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 7684838-Bromo-4-chloro-2-methylquinoline

生成物 1

HCID 225043522-Methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline収率 88.4%

試薬・触媒・溶媒 3

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

反応条件

温度
80 °C

実験手順

Part B: In a mixture of 270 ml dimethoxyethane and 45 ml water, after bubbling through nitrogen gas for 30 minutes, a quantity of 5.0 g ( 19.5 mmol) of 2-methyl-4-chloro-8-bromo-quinoline, 3.5 g (21 mmol) of 2,4,6-trimethyl phenylboronic acid, 13.2 g (42 mmol) Ba(OH)2.8H2O and 0.69 g (0.6 mmol) tetrakis(triphenylphosphine)palladium were subsequently dissolved. After heating to 80° C. for 16 hours and subsequent cooling, 250 ml of water and 500 ml of CH2Cl2 were added. After separation the organic layer was dried over sodium sulphate and concentrated in vacuo. The product was purified on a silicagel column using dichloromethane as eluent. A total of 5.1 g of 2-methyl-4-chloro-8-(2,4,6-trimethylphenyl)-quinoline was obtained (88% yield).

後処理

  1. customafter bubbling through nitrogen gas for 30 minutes
  2. customAfter separation the organic layer
  3. dry with materialwas dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe product was purified on a silicagel column

出典と根拠

ORDレコード
ord-a7fcd8c715fd4e49bef4d0b8ee54a655
出典データセット
uspto-grants-2002_02
特許番号
US06350750B1

関連ノート

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