4-Fluoro-3-phenoxybenzaldehyde → 1-(4-Fluoro-3-phenoxyphenyl)ethanol

HRID 1588886Notes

Reaction equation

HRID 1588886 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[F:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]([OH:10])[CH3:1])=[CH:7][C:6]=1[O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 197548411-(4-Fluoro-3-phenoxyphenyl)ethanolYield 103.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 34 ml (0.10 mole) of methylmagnesium bromide (3.0 M in diethyl ether) in 100 ml of tetrahydrofuran was cooled to 0° C., and 22.0 grams (0.10 mole) of 4-fluoro-3-phenoxybenzaldehyde was slowly added during a 30 minute period. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature at which it was stirred for two hours. At the end of this time the reaction was quenched with aqueous 10% hydrochloric acid, and the reaction mixture was extracted with two 100 ml portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 24.0 grams of 1-(4-fluoro-3-phenoxyphenyl)ethanol. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. customAt the end of this time the reaction was quenched with aqueous 10% hydrochloric acid
  3. extractionthe reaction mixture was extracted with two 100 ml portions of diethyl ether
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0f795b6b6e064e578d98e384474eea36
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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