Phenol → HCID 68380294, compound

HRID 2178710Notes

Reaction equation

HRID 2178710 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1C=O.C1([OH:18])C=CC=CC=1.Br[CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>>[CH3:23][O:22][CH:21]([O:24][CH3:25])[CH2:20][O:18][C:3]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:2]=1[F:1]

Participants

5

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 68380294HCID 68380294, compound

Procedure

2-Fluoro-5-methoxybenzaldehyde was subjected to a Baeyer-Villiger reaction, followed by basic ester hydrolysis. The resulting phenol was reacted with 2-bromo-1,1-dimethoxyethane and potassium carbonate to provide 2-(2,2-dimethoxyethoxy)-1-fluoro-4-methoxybenzene. Cyclization was effected with Amberlyst 15 (see A. Goel and M. Dixit, Synlett 2004, 1990-1994) to afford 7-fluoro-4-methoxy-1-benzofuran, which was demethylated using boron tribromide.

Sources & evidence

ORD record
ord-02d6d248c55c4ae0b18b7546a5501cdd
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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