Dimethylformamide → 4-Fluoro-2-methoxybenzonitrile

HRID 2175842Notes

Reaction equation

HRID 2175842 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:10].CCOC(C)=O.[CH3:17][N:18](C=O)C>[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>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]#[N:18])=[C:3]([O:9][CH3:10])[CH:4]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 70180432-Bromo-5-fluoroanisole

Product 1

HCID 27833294-Fluoro-2-methoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 1-bromo-4-fluoro-2-methoxybenzene (25 g, 0.12 mol) in 250 mL of DMF was added Zn(CN)2 (28.6 g, 0.240 mol) and Pd(PPh3)4 (7.05 g, 6.10 mmol) at one portion and the reaction was charged with Ar and heated to 100° C. for 10 hours. Then the reaction was poured into 1 L of EtOAc and filtered through a kieselguhr pad. The filtrate was washed with water, brine, dried and concentrated to solid, which was purified by silica gel column to give 4-fluoro-2-methoxybenzonitrile.

Workup

  1. additionthe reaction was charged with Ar
  2. filtrationfiltered through a kieselguhr pad
  3. washThe filtrate was washed with water, brine
  4. customdried
  5. concentrationconcentrated to solid, which
  6. customwas purified by silica gel column

Sources & evidence

ORD record
ord-01973d5872944f3e846ac3136cb42060
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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