2-Thiopheneboronic acid → HCID 14789268, compound

HRID 1675506Notes

Reaction equation

HRID 1675506 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O>>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 14789268HCID 14789268, compoundYield 83%

Procedure

Synthesized from 3-bromocyclohex-2-enone and 2-thiophene boronic acid according to the general procedure described for the Suzuki coupling. The product was purified by passing the product through a small silica gel plug eluting with methylene chloride and recrystallization from hexanes and ethyl acetate to yield a pale yellow crystalline solid (125 mg, 83%). 1H NMR (CDCl3, 300 MHz): δ 7.42 (d, J=5.4 Hz, 1H), 7.36 (d, J=3.3 Hz, 1H), 7.08 (t, J=3.9 Hz, 1H), 6.41 (s, 1H), 2.79 (t, J=6.3 Hz, 2H), 2.46 (t, J=6.3 Hz, 2H), 2.14 (quintet, J=6.3 Hz, 2H). 13C NMR (CDCl3, 75 MHz): δ 199.2, 152.3, 142.6, 128.7, 128.2, 127.2, 122.7, 37.3, 28.1, 22.5. LCMS (ESI): mass calcd for (C10H10OS) m/z 178.05; measured [M+H]+: m/z 179.04.

Workup

  1. customThe product was purified
  2. washeluting with methylene chloride and recrystallization from hexanes and ethyl acetate

Sources & evidence

ORD record
ord-a63adb6ac67640e5b25bd3fde7b40d6b
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

Loading…