Allyl bromide → 1-Fluoro-3-methoxy-4-[(2-propenyl)oxy]benzene

HRID 979807Notes

Reaction equation

HRID 979807 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:15][CH:14]=[CH2:13])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 27373684-Fluoro-2-methoxyphenol

Product 1

HCID 202229971-Fluoro-3-methoxy-4-[(2-propenyl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-fluoro-2-methoxyphenol (27.0 g) in DMF (50 ml) was added dropwise to a mixture of 60% NaH (7.0 g) in DMF (250 ml). After stirring the reaction for 1 hour, allylbromide (21.0 ml) was added and stirring was continued for 1 hour at room temperature. The reaction was poured onto ice/water and extracted with ethyl acetate. The organic layer was separated, dried and evaporated to afford the desired compound.

Workup

  1. customthe reaction for 1 hour
  2. stirringstirring
  3. additionThe reaction was poured onto ice/water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ee58450110184ee4acd450103dcb50a1
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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