Acetic Acid → HCID 67257632, compound

HRID 1192701Notes

Reaction equation

HRID 1192701 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:4]([N+:17]([O-])=O)[C:3]=1[CH:20]=[O:21].C(O)(=O)C.Cl>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2=[CH:20][O:21][N:17]=[C:4]2[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:6]([CH2:8][OH:9])[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 86656184HCID 86656184, compound

Product 1

HCID 67257632HCID 67257632, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-chloro-3′-fluoro-6-(hydroxymethyl)-2-nitrobiphenyl-3-carbaldehyde (0.50 g, 1.6 mmol), acetic acid (4 mL), and conc. HCl (4 mL) was added stannous chloride, dihydrate (1.4 g, 6.4 mmol). After stirring at room temperature for 2 hours, the resulting mixture was diluted with ethyl acetate, washed with water, brine, and then dried with sodium sulfate and concentrated to dryness. The residue was purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the desired product (0.104 g, 23%). LCMS calculated for C14H10ClFNO2 (M+H)+: m/z=278.0; Found: 278.0.

Workup

  1. washwashed with water, brine
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe residue was purified on silica gel
  5. washeluting with 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0f8b75454aad4b33b670626a984431e0
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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