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

HRID 1700116노트

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HRID 1700116 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a7fcd8c715fd4e49bef4d0b8ee54a655
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350750B1

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