Dimethylformamide → 3-Cyano-6-((4-methoxybenzyl)oxy)benzaldehyde

HRID 1700285

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:20][N:21](C=O)C>[NH4+].[OH-].[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([C:2]1[CH:3]=[C:4]([C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1)[CH:5]=[O:6])#[N:21]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-bromo-6-((4-methoxybenzyl)oxy)benzaldehyde (4 g), Zn(CN)2 (1 g) and Pd(PPh3)4 (4.32 g) in 40 mL DMF was stirred at 90° C. for 3 hours, cooled to ambient temperature and diluted with 100 mL 50% NH4OH. The aqueous layer was extracted with ethyl acetate (3×). The organic layer was dried, concentrated and purified on silica gel column (ethyl acetate/hexane, 1:4) to afford 2.8 g of 3-cyano-6-((4-methoxybenzyl)oxy)benzaldehyde as a yellow solid.

Workup

temperaturecooled to ambient temperature
extractionThe aqueous layer was extracted with ethyl acetate (3×)
customThe organic layer was dried
concentrationconcentrated
custompurified on silica gel column (ethyl acetate/hexane, 1:4)

Sources & evidence

ORD record: ord-549a0c946ffd431295794754bc60789d
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350761B1

Linked notes

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