4-Fluorophenol → HCID 12531880, compound

HRID 1704070Notes

Reaction equation

HRID 1704070 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 10942334Sodium MethoxideHCID 20392602HCID 20392602, compound

Product 1

HCID 12531880HCID 12531880, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2.7 g of p-fluorophenol in 20 ml of methanol was added 1.89 g of sodium methoxide. To the solution was added 7.98 g of methyl α-bromo-α-[p-(p-methylsulfonylphenoxy)phenyl]acetate in 40 ml of methanol. The mixture was refluxed and stirred for 18 hours, chilled and filtered to give 4.3 g of white crystals, mp 135°-137° C. Recrystallization from acetone-hexane gave the product as white crystals, mp 136°-138° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturechilled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-32e32b4a1a97416a882761f7cd3c442f
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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