Hydrochloric Acid → HCID 86753553, compound

HRID 342424

Reaction equation

HRID 342424 reaction equation
[CH3:1][C:2]1[O:6][C:5]2[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:4]=2[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:18][C:19]([F:27])([F:26])[C:20]([C:22]([F:25])([F:24])[F:23])=[O:21].O.O.O.FC(F)(F)C(C(F)(F)F)=O.S(=O)(=O)(O)O.Cl>ClCCl>[OH:21][C:20]([C:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:5]=2[O:6][C:2]=1[CH3:1])([C:22]([F:25])([F:24])[F:23])[C:19]([F:27])([F:26])[F:18]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 12695HexafluoroacetoneHCID 36719Hexafluoroacetone trihydrateHCID 6451240Aluminum(III) ChlorideHCID 132018972-Methyl-7-nitrobenzofuran

Product 1

HCID 86753553HCID 86753553, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a mixture of 2-methyl-7-nitrobenzo[b]furan (200 mg) and aluminum chloride (301 mg) in dichloromethane was passed hexafluoroacetone gas which was made from hexafluoroacetone trihydrate (4.7 ml) and conc. sulfuric acid (15 ml). The mixture was stirred at ambient temperature for 4 hours and then, cooled to 4° C. To the mixture was added 1N-hydrochloric acid dropwise. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from n-hexane to give 3-(1-hydroxy-2,2,2-trifluoro-1-trifluoromethylethyl)-2-methyl-7-nitrobenzo[b]furan (265 mg).

Workup

  1. temperaturecooled to 4° C
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. customthe obtained oil was crystallized from n-hexane

Sources & evidence

ORD record
ord-9ad3bf85b765418e9a85d1c8f96c856a
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Linked notes

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