Benzaldehyde → HCID 117599874, compound

HRID 513239Notes

Reaction equation

[C:1]1([Mg]Br)[CH:6]=[CH:5]C=[CH:3][CH:2]=1.C(OCC)C.[CH2:14]([O:16][C:17](=[O:27])[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[C:20]([CH3:25])[C:19]=1I)[CH3:15].[Li+].[Cl-].C(=O)C1C=CC=CC=1>C1COCC1.[Cl-].[NH4+]>[Br:24][C:21]1[C:20]([CH3:25])=[C:19]2[C:18](=[CH:23][CH:22]=1)[C:17](=[O:27])[O:16][CH:14]2[C:15]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

3M PhMgBr in diethyl ether (1.7 mL, 5.07 mmol, 1.1 eq.) is added dropwise to the solution of 4-Bromo-2-iodo-3-methyl-benzoic acid ethyl ester (1.7 g, 4.61 mmol), LiCl (195 mg, 4.61 mmol) in dry THF (50 mL) at −10° C. The mixture is stirred at −10° C. for 2 hours. Benzaldehyde (0.977 g, 9.22 mmol) is slowly added to mixture at −10° C. This solution is stirred at room temperature for 16 hours and diluted with saturated aqueous ammonium chloride solution (100 mL). This solution is extracted with ethyl acetate (3×70 mL). The combined organic layers are washed with water and brine, dried over anhydrous sodium sulfate, concentrated in vacuo. The residue is purified by a silica chromatography to give the desire compound as a white solid.

Workup

stirringThis solution is stirred at room temperature for 16 hours
extractionThis solution is extracted with ethyl acetate (3×70 mL)
washThe combined organic layers are washed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue is purified by a silica chromatography

Sources & evidence

ORD record: ord-aaacb8f722bd4237a448338eb9c356eb
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102684B2

Reaction notes

Loading…