Potassium Hydroxide → HCID 23089558, compound

HRID 2378519Notes

Reaction equation

HRID 2378519 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[K+].[F:11][C:12]([F:22])([F:21])[C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>CO>[F:11][C:12]([F:21])([F:22])[C:13]1[CH:20]=[CH:19][C:16]([CH2:17][S:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 2401474-Mercaptophenol

Product 1

HCID 23089558HCID 23089558, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

10 ml of methanol solution containing 2.8 g of 4-mercaptophenol was dropped with ice cooling into 20 ml of methanol solution containing 1.4 g of potassium hydroxide, followed by further stirring for 30 minutes. To this reaction mixture, 10 ml of methanol solution containing 5.0 g of 4-trifluoromethyl benzyl bromide was added with ice cooling, followed by stirring for 18 hours at room temperature. After concentrating the reaction mixture, ethyl acetate and water were added, followed by fractionating an organic layer. After the organic layer was dried with anhydrous magnesium sulfate, it was concentrated. The concentrate was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate/gradation) to produce 2.23 g of the desired product.

Workup

  1. additionwas added with ice cooling
  2. stirringby stirring for 18 hours at room temperature
  3. concentrationAfter concentrating the reaction mixture, ethyl acetate and water
  4. additionwere added
  5. dry with materialAfter the organic layer was dried with anhydrous magnesium sulfate, it
  6. concentrationwas concentrated
  7. customThe concentrate was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate/gradation)

Sources & evidence

ORD record
ord-b4575b0c6846463fb747c7359647b98e
Source dataset
uspto-grants-2008_12
Patent number
US07470803B2

Reaction notes

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