2-Ethyl-1-butanol → 1-Bromo-3-(2-ethylbutoxy)benzene

HRID 875530

반응식

HRID 875530 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([CH:11]([CH2:14][CH3:15])[CH2:12]O)[CH3:10]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:12][CH:11]([CH2:14][CH3:15])[CH2:9][CH3:10])[CH:3]=1

참가 물질

3

반응물 2

HCID 73582-Ethyl-1-butanolHCID 115633-Bromophenol

생성물 1

HCID 673177401-Bromo-3-(2-ethylbutoxy)benzene

실험 절차

Coupling of 3-bromophenol (17) (5.0 g, 28.9 mmol) with 2-ethylbutan-1-ol (3.25 g, 31.79 mmol) was conducted following the procedure given for Example 6. The reaction mixture was concentrated under reduced pressure then triturated with diethyl ether. The suspension was filtered and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (100% hexanes) gave 1-bromo-3-(2-ethylbutoxy)benzene a clear liquid. Yield (5.04 g, 62%): 1H NMR (400 MHz, DMSO-d6) δ 7.20 (t, J=8.0 Hz, 1H), 7.11 (t, J=2.2 Hz, 1H), 7.07 (dd, J=8.0, 2.0 Hz, 1H), 6.92 (dd, J=8.4, 2.6 Hz, 1H), 3.84 (d, J=5.6 Hz, 2H), 1.61-1.53 (m, 1H), 1.46-1.30 (m, 4H), 0.86 (t, J=7.4 Hz, 6H).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthen triturated with diethyl ether
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification by flash chromatography (100% hexanes)

출처 및 근거

ORD 기록
ord-2f71717abc794c0db2aa3950fd35ae8d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981153B2

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