2,3,5-Trimethylphenol → 1-[2-(4-Bromophenyl)ethoxy]-2,3,5-trimethylbenzene

HRID 33030

반응식

HRID 33030 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 127692,3,5-TrimethylphenolHCID 13831TributylphosphineHCID 728512-(4-Bromophenyl)ethanol

생성물 1

HCID 674216101-[2-(4-Bromophenyl)ethoxy]-2,3,5-trimethylbenzene수율 73%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 2-(4-bromophenyl)ethanol (20.0 mL, 143 mmol), 2,3,5-trimethylphenol (31.1 g, 229 mmol), azodicarboxylic dipiperidide (72.1 g, 286 mmol) and tributylphosphine (88 mL; 357 mmol) in toluene (2.00 L) was heated to reflux for 2 h. The mixture was allowed to cool to rt. The mixture was filtered, washed with toluene and the solvents were partially removed under reduced pressure. The residue was diluted with Et2O and washed with aq. 1M NaOH (2×). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (petroleum ether→Et2O/petroleum ether 1:3) yielded the title compound (33.1 g, 73%). LC-MS: Rt=6.95.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. filtrationThe mixture was filtered
  4. washwashed with toluene
  5. customthe solvents were partially removed under reduced pressure
  6. additionThe residue was diluted with Et2O
  7. washwashed with aq. 1M NaOH (2×)
  8. dry with materialextracts were dried over MgSO4
  9. filtrationfiltered
  10. customthe solvents were removed under reduced pressure
  11. customPurification of the residue by FC (petroleum ether→Et2O/petroleum ether 1:3)

출처 및 근거

ORD 기록
ord-cbe262c4c9014bdc9e0c5fefc4472d11
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427613B2

연결된 노트

불러오는 중…