3-Bromo-6-methoxy-2-methylbenzonitrile → 3-Acetyl-6-methoxy-2-methylbenzonitrile

HRID 1466072Notes

Reaction equation

HRID 1466072 reaction equation
Br[C:2]1[C:3]([CH3:12])=[C:4]([C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)[C:5]#[N:6].C(CCCC[Sn]([O:28][CH2:29][CH3:30])(CCCC)CCCC)=C>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.C1(C)C=CC=CC=1>[C:29]([C:2]1[C:3]([CH3:12])=[C:4]([C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)[C:5]#[N:6])(=[O:28])[CH3:30]

Participants

5

Reactant 2

HCID 675160643-Bromo-6-methoxy-2-methylbenzonitrileHCID 131732685Vinyl ethoxy tributyltin

Product 1

HCID 895249033-Acetyl-6-methoxy-2-methylbenzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a 20 mL microwave tube was added a stir bar, 3-bromo-6-methoxy-2-methylbenzonitrile (4.0 g, 18 mmol), vinyl ethoxy tributyltin (9.5 g, 26 mmol), palladium tetrakis (1.0 g, 0.88 mmol), and anhydrous toluene (15 mL). The tube was capped, degassed and purged with N2. The reaction mixture was heated to 110° C. for 12 hours. The tube was cooled to room temperature and treated with 4 M HCl (10 mL) and stirred for 1 hour. The crude product was extracted with EtOAc. The extraction was washed with brine, dried with Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (Hexanes:EtOAc=1:1) to afford the title product.

Workup

  1. additionTo a 20 mL microwave tube was added a stir bar
  2. customThe tube was capped
  3. customdegassed
  4. custompurged with N2
  5. temperatureThe tube was cooled to room temperature
  6. additiontreated with 4 M HCl (10 mL)
  7. extractionThe crude product was extracted with EtOAc
  8. extractionThe extraction
  9. washwas washed with brine
  10. dry with materialdried with Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe crude residue was purified by silica gel column chromatography (Hexanes:EtOAc=1:1)

Sources & evidence

ORD record
ord-bf426be040f04334b00357810916ae6e
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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