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

HRID 74357

반응식

HRID 74357 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-43e68112a7e5497784c2a5353ee7bb7c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829244B2

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