(2H-1,3-benzodioxol-5-yl)boronic acid → HCID 13354023, compound

HRID 1675512Notes

Reaction equation

HRID 1675512 reaction equation
Br[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[CH2:9]1[O:17][C:16]2[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][C:11]=2[O:10]1>>[O:17]1[C:16]2[CH:15]=[CH:14][C:13]([C:2]3[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=3)=[CH:12][C:11]=2[O:10][CH2:9]1

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 109650383-Bromocyclohex-2-enone

Product 1

HCID 13354023HCID 13354023, compoundYield 85%

Procedure

Synthesized from 3-bromocyclohex-2-enone and 3,4-methylenedioxyphenylboronic acid according to the general procedure described for the Suzuki coupling. Purification by automated flash chromatography using gradient elution (0 to 80% ethyl acetate/hexanes) yielded the product (164 mg, 85%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.07-7.00 (m, 2H), 6.81 (d, J=8.0 Hz, 2H), 6.31 (s, 1H), 5.99 (s, 2H), 2.70 (t, J=5.5 Hz, 2H), 2.45 (t, J=6.3 Hz, 2H), 2.12 (quintet, J=6.3 Hz, 2H). 13C (75 MHz, CDCl3): 199.7, 159.0, 149.2, 148.2, 132.8, 124.2, 120.7, 108.4, 106.3, 101.6, 37.4, 28.3, 23.0. LCMS (ESI): mass calcd for (C13H12O3) m/z 216.08; measured [M+H]+: m/z 216.95.

Workup

  1. customPurification by automated flash chromatography
  2. washelution (0 to 80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8067ae5d589c451e860986313d16f720
Source dataset
uspto-grants-2011_08
Patent number
US08003692B2

Reaction notes

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