Water → 2-CYCLOPROPYLBENZALDEHYDE

HRID 888965Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:10]1(B(O)O)[CH2:12][CH2:11]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(C)C=CC=CC=1.O>C(OCC)(=O)C.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:10]1([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

A 60 mL reaction vial is charged with 2-bromo-benzaldehyde (10.810 mmoles, 1.264 mL), cyclopropylboronic acid (14.053 mmoles, 1.207 g), potassium phosphate tribasic N-hydrate (37.834 mmoles, 8.031 g), tricyclohexylphosphine (1.081 mmoles, 303.139 mg), toluene (283.654 mmoles, 30.000 mL), and water (83.263 mmoles, 1.500 mL). The mixture is then thoroughly degassed. Next, Pd(OAc)2 (540.482 μmoles, 121.343 mg) is added and the mixture is placed under nitrogen and heated to 100° C. After 2 hours, cool to room temperature and dilute with ethyl acetate (50 mL) and brine (50 mL). Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under reduced pressure. Purify by silica gel chromatography eluting with hexanes: dichloromethane 20-50% to afford the title compound. 1H NMR (400.31 MHz, cdcl3): 10.57 (s, 1H), 7.78 (dd, J=1.3, 7.9 Hz, 1H), 7.45 (td, J=7.5, 1.3 Hz, 1H), 7.28 (t, J=7.5 Hz, 1H), 7.09 (d, J=7.9 Hz, 1H), 2.63-2.56 (m, 1H), 1.07-1.02 (m, 2H), 0.77-0.73 (m, 2H).

Workup

customA 60 mL reaction
customThe mixture is then thoroughly degassed
temperaturecool to room temperature
dry with materialDry the organic layer over anhydrous sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customPurify by silica gel chromatography
washeluting with hexanes

Sources & evidence

ORD record: ord-3ec5bf50aeb2406e9def40d61dcf7655
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252798B2

Reaction notes

Loading…