تفاعل #161539

ord-43e68112a7e5497784c2a5353ee7bb7c

معادلة التفاعل

Oc1cccc(Br)c1
3-bromophenol
CCC(CC)CO
2-ethylbutan-1-ol
CCC(CC)COc1cccc(Br)c1
1-bromo-3-(2-ethylbutoxy)benzene

المتفاعلات

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزThe reaction mixture was concentrated under reduced pressure
  2. 2
    أخرىthen triturated with diethyl ether
  3. 3
    ترشيحThe suspension was filtered
  4. 4
    تركيزthe filtrate was concentrated under reduced pressure
  5. 5
    أخرىPurification by flash chromatography (100% hexanes)

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08829244B2uspto-grants-2014_09