Dimethylformamide → 5-Formyl-2-(trifluoromethoxy)benzonitrile

HRID 2269250Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]([F:14])([F:13])[F:12])[CH:5]=[O:6].[CH3:15][N:16](C=O)C>C1(C)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N.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:15]([C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]([F:14])([F:13])[F:12])[CH:5]=[O:6])#[N:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred suspension of Compound 19 (6.85 g, 21.7 mmol) and zinc cyanide (4.07 g, 34.7 mmol) in dry DMF (35 ml) was added tetrakis(triphenylphosphine)palladium(0) (3.00 g, 2.60 mmol) portionwise at room temperature. The reaction mixture was heated at 100° C. for 9 h. The reaction mixture was diluted with toluene (100 ml)-2M NH3 aq. (100 ml). The organic layer was separated. The aqueous layer was diluted with toluene (100 ml), filtered through a pad of celite and the filter cake was washed with toluene. The organic layer was separated and the aqueous layer was extracted with toluene. The combined solution was washed with 2M NH3 aq. (50 ml) and brine, dried (MgSO4), and concentrated in vacuo to give crude product as a dark tan oil.

Workup

customThe organic layer was separated
additionThe aqueous layer was diluted with toluene (100 ml)
filtrationfiltered through a pad of celite
washthe filter cake was washed with toluene
customThe organic layer was separated
extractionthe aqueous layer was extracted with toluene
washThe combined solution was washed with 2M NH3 aq. (50 ml) and brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto give crude product as a dark tan oil

Sources & evidence

ORD record: ord-88542c3d4a20409d8e1c9aed903c1f7c
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329396B1

Reaction notes

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