Water → HCID 12531888, compound

HRID 1863341Notes

Reaction equation

HRID 1863341 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:26]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:29][CH:30]=2)=[CH:20][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15].O>CO.C1C=CC=CC=1.[I-].[K+]>[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:26]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:29][CH:30]=3)=[CH:20][CH:19]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 10942334Sodium MethoxideHCID 20392575Methyl alpha-bromo-alpha-[p-(alpha,alpha,alpha-trifluoro-m-tolyloxy)phenyl]acetate

Product 1

HCID 12531888HCID 12531888, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 2.8 g of p-fluorophenol, 1.19 g of sodium methoxide, and 50 mg of potassium iodide in 40 ml of methanol was added 7.62 g of methyl α-bromo-α-[p-(α,α,α-trifluoro-m-tolyloxy)phenyl]acetate in 10 ml of benzene. The mixture was refluxed overnight and cooled to room temperature. The mixture was poured into 100 ml of water and extracted with 2×75 ml of ether. The combined extracts were washed with 50 ml of 5% NaOH, 2×50 ml of water, 50 ml of saturated brine and dried (MgSO4). Evaporation of the solvent at reduced pressure yielded an amber oil which was chromatographed on 100 g of silica gel (benzene) to yield 6.7 g of an amber oil which solidified on trituration with petroleum ether, mp 70°-72.5° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionextracted with 2×75 ml of ether
  3. washThe combined extracts were washed with 50 ml of 5% NaOH, 2×50 ml of water, 50 ml of saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent at reduced pressure
  6. customyielded an amber oil which
  7. customwas chromatographed on 100 g of silica gel (benzene)

Sources & evidence

ORD record
ord-e3e7893f7adf451795d8769b71984c74
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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