(3-hydroxyphenyl)boronic Acid → HCID 24747222, compound

HRID 1675513Notes

Reaction equation

HRID 1675513 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[OH:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1>>[OH:8][C:4]1[CH:3]=[C:2]([C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:9])[CH:15]=2)[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 24747222HCID 24747222, compoundYield 64%

Procedure

Synthesized from 3-bromocyclohex-2-enone and 3-hydroxyphenylboronic acid according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography yielded the product (83 mg, 64%) as a pale yellow solid. 1H NMR (300 MHz, CD3OD): δ 7.22 (t, J=7.8 Hz 1H), 7.05 (ddd, J=7.8, 1.5, 0.9 Hz, 1H), 6.98 (t, J=1.5 Hz, 1H), 6.83 (ddd, J=8.1, 2.4, 1.2 Hz, 1H), 6.31 (t, J=1.2 Hz, 1H), 2.79 (td, J=6.0, 1.5 Hz, 2H), 2.46 (t, J=6.0 Hz, 2H), 2.12 (quintet, J=6.6 Hz, 2H). 13C (75 MHz, CD3OD): 202.5, 163.4, 158.8, 141.3, 130.7, 125.2, 118.4, 118.2, 113.8, 38.1, 29.2, 23.9. LCMS (ESI): mass calcd for (C12H12O2) m/z 188.08; measured [M+H]+: m/z 189.0.

Workup

  1. customPurification by automated flash chromatography

Sources & evidence

ORD record
ord-f9effb63e8bc4b6f82435c892cd8acf8
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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