Hydrochloric Acid → 2'-Fluorobiphenyl-3-carboxylic acid

HRID 1731803Notes

Reaction equation

HRID 1731803 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1.[Mn]([O-])(=O)(=O)=[O:16].[K+].S(=O)(O)[O-].[Na+].Cl.[OH2:27]>C(O)(C)(C)C.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[C:14]([OH:16])=[O:27]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 516875Potassium Permanganate2×HCID 128530412-Fluoro-3'-methyl-1,1'-biphenylHCID 23665763Sodium Bisulfite

Product 1

HCID 27826832'-Fluorobiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7.0 g 3-(2-fluorophenyl)-toluene and 29.5 g potassium permanganate in 500 ml t-butanol and 100 ml water was heated at 90° C. for 18 hours. The reaction mixture was cooled to room temperature, sufficient sodium bisulfite was added to dissolve the remaining potassium permanganate and manganese dioxide, and the pH was adjusted to 1 with hydrochloric acid. The resulting precipitate was collected by filtration, redissolved in ethyl acetate and this solution was dried and evaporated yielding the product as a white solid of m.p. 147°-148° C. after recrystallization from hexanes (5.7 g, 70% yield). NMR (DMSO-d6, 250 MHz): 8.2-7.3 (m, 8H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. dissolutionredissolved in ethyl acetate
  4. customthis solution was dried
  5. customevaporated

Sources & evidence

ORD record
ord-56c6ddec21f640c8814e715ec24ceacc
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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