Allyl bromide → Phenol, 2-fluoro-6-(2-propenyl)- (9CI)
Reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11])C=C.F[C:13]1[CH:18]=CC=C[C:14]=1O.C(Br)C=C>CCOCC>[CH2:18]([C:10]1[C:5]([OH:4])=[C:6]([F:11])[CH:7]=[CH:8][CH:9]=1)[CH:13]=[CH2:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Other workers have prepared o-fluorophenyl allyl ether in a 90.5-93% yield from o-fluorophenol and allyl bromide. Thereafter using a thermal Claisen rearrangement of the ether gave 6-allyl-2-fluorophenol in an 80% yield. However, attempts to oxidize this last named compound to 3-fluorosalicylaldehyde using dichromate solutions gave no reproducible results, i.e., a 55% yield from the first experiment but less than 5% in subsequent runs.
Sources & evidence
- ORD record
- ord-71971db66e674abea95ff5d83eff0965
- Source dataset
- uspto-grants-1978_11
- Patent number
- US04124643
Reaction notes
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