Thiophene-3-boronic acid → HCID 10866911, compound

HRID 1675505Notes

Reaction equation

HRID 1675505 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][C:11](B(O)O)=[CH:10]1>>[S:9]1[CH:13]=[CH:12][C:11]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)=[CH:10]1

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 10866911HCID 10866911, compoundYield 72%

Procedure

Synthesized from 3-bromocyclohex-2-enone and 3-thiophene boronic acid according to the general procedure described for the Suzuki coupling. The product was purified by automated flash chromatography using gradient elution (0 to 50% ethyl acetate/hexanes). A yellow solid was isolated after collection of fractions and recrystallized from hexanes and ethyl acetate to give 0.086 g of colorless needles (72%). 1H NMR (CDCl3, 300 MHz): δ 2.13 (quintet, J=6.3 Hz, 2H), 2.47 (t, J=6.3 Hz, 2H), 2.76 (dd, J=6.3, 1.2 Hz, 2H), 6.39 (t, J=1.2 Hz, 1H), 7.31-7.36 (m, 2H), 7.55 (dd, J=2.7, 1.5 Hz, 1H). 13C NMR (CDCl3, 75 MHz): δ 22.6, 27.8, 37.4, 123.8, 124.9, 125.0, 126.6, 140.5, 153.3, 199.9. LCMS (ESI): mass calcd for (C10H10OS) m/z 178.05; measured [M+H]+: m/z 179.04.

Workup

  1. customThe product was purified by automated flash chromatography
  2. washelution (0 to 50% ethyl acetate/hexanes)
  3. customA yellow solid was isolated
  4. customafter collection of fractions
  5. customrecrystallized from hexanes and ethyl acetate

Sources & evidence

ORD record
ord-3886787a23eb429cae75af04864e3308
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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