Hydrochloric Acid → HCID 66817593, compound

HRID 1755096Notes

Reaction equation

HRID 1755096 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH:24]=[CH2:25].Cl>CN(C=O)C>[CH2:22]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=[C:2]([O:1][CH2:9][CH2:10][CH:2]=[CH2:3])[CH:3]=1)[CH2:23][CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 27831463-hydroxy-5-(trifluoromethyl)benzoic Acid

Product 1

HCID 66817593HCID 66817593, compoundYield 158.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-5-trifluoromethyl-benzoic acid (2.17 g, 10.6 mmol), potassium carbonate (8.73 g, 63.2 mmol) and 4-bromo-1-butene (4.34 ml, 43.7 mmol) were dissolved in DMF (21 ml), and this mixture was irradiated in a microwave apparatus (100° C., 60 min). The reaction solution was poured into a cooled aqueous dilute hydrochloric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to give 3-but-3-enyloxy-5-trifluoromethyl-benzoic acid but-3-enyl ester (2.64 g, 80%).

Workup

  1. customthis mixture was irradiated in a microwave apparatus (100° C., 60 min)
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a3b19976ad594d329bec8ad4c9c1a54c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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