Allyl bromide → HCID 18512342, compound

HRID 1370818Notes

Reaction equation

HRID 1370818 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11](Br)[CH:12]=[CH2:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:13]([O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[CH:12]=[CH2:11]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 18512342HCID 18512342, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Fluoro-4-hydroxybenzonitrile (5.00 g, 36.5 mmoles) and allyl bromide (3.47 mL, 40.1 mmoles) in anhydrous DMF (40 mL) were treated with K2CO3 (10.0 g, 72.9 mmoles) and stirred overnight at 80° C. Reaction mixture cooled and diluted with ethyl acetate, washed with H2O (2×) and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to provide the title compound with no further purification.

Workup

  1. customReaction mixture
  2. temperaturecooled
  3. washwashed with H2O (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4a3c56e7fe5461db4ce22c2097dbd61
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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