1-Bromo-2-iodobenzene → 1-Bromo-2-(3-methyl-butyl)-benzene

HRID 1436515노트

반응식

HRID 1436515 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[CH3:9][CH:10]([CH3:14])[CH2:11][CH2:12][Zn]>C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[Br:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:12][CH2:11][CH:10]([CH3:14])[CH3:9]

참가 물질

4

반응물 2

HCID 114151-Bromo-2-iodobenzeneHCID 178445878HCID 178445878, 화합물

생성물 1

HCID 210637691-Bromo-2-(3-methyl-butyl)-benzene수율 78.1%

시약·촉매·용매 1

HCID 72499888Dibenzalacetone palladium촉매

실험 절차

Charge a Schlenck flask with palladium dibenzylidene acetone (88 mg, 0.16 mmol) and tri-o-furyl phosphine (72 mg, 0.31 mmol), purge with nitrogen and add 2 ml of dry THF. Stir until the deep purple solution turns to greenish yellow and add 1-iodo-2-bromobenzene (0.8 ml. 6.2 mmol) followed by 3-methyl-butyl zinc (0.5 M solution in THF, 30 ml, 15 mmol). Stir at room temperature for 4 hours. Add silica gel, concentrate under reduced pressure, load residue onto a flash silica gel column, and elute with hexane to obtain the desired compound as a colorless liquid (1.1 g, 75%).

후처리

  1. custompurge with nitrogen
  2. additionadd 2 ml of dry THF
  3. stirringStir at room temperature for 4 hours
  4. concentrationAdd silica gel, concentrate under reduced pressure, load residue onto a flash silica gel column
  5. washelute with hexane

출처 및 근거

ORD 기록
ord-b1b6099751cc47d8949288db107aa918
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618978B2

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