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

HRID 74357

反応式

HRID 74357 の反応式
[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

参加物

3

反応物 2

HCID 73582-Ethyl-1-butanolHCID 115633-Bromophenol

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-43e68112a7e5497784c2a5353ee7bb7c
出典データセット
uspto-grants-2014_09
特許番号
US08829244B2

関連ノート

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