Hydrochloric Acid → 7,8-Difluoro-3-trimethylsilanylnaphthalen-2-ol

HRID 1873320Notes

Reaction equation

HRID 1873320 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10](Cl)=[O:11].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19].Cl>ClCCl>[F:8][C:7]1[C:2]([F:1])=[C:3]2[C:4]([CH:22]=[C:21]([Si:18]([CH3:20])([CH3:19])[CH3:17])[C:10]([OH:11])=[CH:9]2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 66111TrimethylsilylacetyleneHCID 6451240Aluminum(III) ChlorideHCID 25110985(2,3-Difluorophenyl)acetyl chloride

Product 1

HCID 581519377,8-Difluoro-3-trimethylsilanylnaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 50.0 g (0.26 mol) of 2,3-difluorophenylacetyl chloride in 100 ml of dichloromethane is slowly added to a suspension of 71.5 g (0.53 mol) of aluminium(III) chloride in 300 ml of dichloromethane at −20° C. After 30 min at this temperature, trimethylsilylacetylene is metered in, and the mixture is stirred for 30 min. The batch is added to ice-water and acidified using hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed successively with sat. sodium hydrogencarbonate soln. and sat. sodium chloride soln. The solution is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:ethyl acetate=9:1), giving 7,8-difluoro-3-trimethylsilanylnaphthalen-2-ol as a brown oil.

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe combined organic phases are washed successively with sat. sodium hydrogencarbonate soln
  4. customThe solution is dried
  5. customevaporated to dryness
  6. customThe residue is purified by column chromatography (SiO2, n-heptane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8b64526dadaa44299e7f2fcf7c9ca7ba
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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