Hydrochloric Acid → 3-{4-[(3,4-Difluorophenyl)methoxy]phenyl}prop-2-enoic acid

HRID 2184364Notes

Reaction equation

HRID 2184364 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([OH:12])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23]Br.[OH-].[Na+].Cl>C1COCC1.CC(CC)=O>[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23][O:12][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:1][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 637542P-Coumaric Acid

Product 1

HCID 533963793-{4-[(3,4-Difluorophenyl)methoxy]phenyl}prop-2-enoic acidYield 73.4%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2.5 g (15.2 mmol) p-cumaric acid is dissolved 100 ml ethyl methyl ketone. 4.21 g (30.5 mmol) potassium carbonate and 6.31 g (30.5 mmol) 3,4-difluorobenzyl bromide are added and the reaction mixture is hold at 70° C. over night. Dilution with water and extraction with ethyl acetate leaves a solid which is recrystallised from diethyl ether/n-hexane. The crude ester so obtained is dissolved in 100 ml THF and treated with 30.5 ml (30.5 mmol) of an aqueous 1 N sodium hydroxide solution. The mixture is heated to 50° C. for 6 hours, cooled and acidified with 1 N hydrochloric acid. The precipitate is filtered off and dried to yield 3.24 g (73%) of a colorless solid. MS: m/e=288.9 (M−H).

Workup

  1. customat 70° C.
  2. extractionDilution with water and extraction with ethyl acetate
  3. customleaves a solid which
  4. customis recrystallised from diethyl ether/n-hexane
  5. customThe crude ester so obtained
  6. temperaturecooled
  7. filtrationThe precipitate is filtered off
  8. customdried

Sources & evidence

ORD record
ord-0cca05ccb49b422fbb6117c89a724d16
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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