Hydrochloric Acid → HCID 69518001, compound

HRID 855098Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4](OC)[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[C:13]([O-])([O-])=O.[K+].[K+].C(N(CC)CC)C.[F:26][C:27]([F:36])([F:35])/[CH:28]=[CH:29]/[C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl>CS(C)=O>[Br:1][C:2]1[CH:9]=[C:6]2[C:5](=[C:4]([CH3:13])[CH:3]=1)[O:10][CH:28]([C:27]([F:35])([F:36])[F:26])[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:7]2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (1.40 g, 6.51 mmole), K2CO3 (1.80 g, 13.02 mmole), triethylamine (2.63 g, 26.05 mmole), and ethyl 4,4,4-trifluorocrotonate (4.38 g, 26.05 mmole) in anhydrous DMSO (5.0 mL) was heated to 90 ° C. under a dry N2 atmosphere for 18 hrs. The contents were poured into 2.4 N HCl (50 ml) and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give a dark yellow oil which was subject to flash chromatography (silica gel) and eluted with 10% EtOAc in hexanes to give a yellow solid (1.6 g, 68%). GCMS m/z 364.0 (M+). 1H NMR (CDCl3/400 MHz) 7.59 (s, 1H), 7.27 (s, 1H), 7.16 (s, 1H), 5.70 (q, 1H, J=7.0 Hz), 4.29 (m, 2H), 2.19 (s, 3H), 1.32 (m, 3H).

Workup

extractionextracted with EtOAc (2×100 mL)
washThe combined extracts were washed with brine (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a dark yellow oil which
washeluted with 10% EtOAc in hexanes

Sources & evidence

ORD record: ord-846137cac38347219bc0c22e400279a3
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

Loading…