Hydrochloric Acid → 3,4-Difluorophenoxymethyl vinyl ketone

HRID 1106596Notes

Reaction equation

HRID 1106596 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[O:5][CH2:6][C:7]([OH:9])=O.[CH2:14]1COC[CH2:15]1.C([Mg]Br)=C.Cl>COCCOC>[CH:14]([C:7]([CH2:6][O:5][C:4]1[CH:10]=[CH:11][C:12]([F:13])=[C:2]([F:1])[CH:3]=1)=[O:9])=[CH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 3029152-(3,4-Difluorophenoxy)acetic acidHCID 178418507HCID 178418507, compound

Product 1

HCID 221142323,4-Difluorophenoxymethyl vinyl ketone

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 3,4-difluorophenoxy acetic acid (5.00 g, 25.7 mmol) lithium salt in DME (20 mL) was added to a 1M THF solution of vinyl magnesium bromide (38 mmol). After a period of 18h, the resulting clear solution was poured over 1N HCl (67 mL). The aqueous phase was then extracted with Et2O. The ethereal phase was washed with H2O, 1M K2CO3 then H2O. After drying over MgSO4 and evaporation an orange oil was obtained and used as such for the next step.

Workup

  1. extractionThe aqueous phase was then extracted with Et2O
  2. washThe ethereal phase was washed with H2O, 1M K2CO3
  3. dry with materialAfter drying over MgSO4 and evaporation an orange oil
  4. customwas obtained

Sources & evidence

ORD record
ord-86f1bbfdacaa4436affe9766b5682083
Source dataset
uspto-grants-2000_05
Patent number
US06057319

Reaction notes

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