1-(4'-Fluoro(1,1'-biphenyl)-4-yl)ethanone → 4-(4-Fluorophenyl)benzoic acid

HRID 2101232

Reaction equation

HRID 2101232 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])C)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[O:17](Br)[Na].C(O)(=O)C.C1(C2C=CC=CC=2)C=CC=CC=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:17])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6081141-(4'-Fluoro(1,1'-biphenyl)-4-yl)ethanoneHCID 656671Sodium PyrosulfiteHCID 21957439HCID 21957439, compoundHCID 178507097sodium hypobromite

Product 1

HCID 27826894-(4-Fluorophenyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

NaOH (7 g) was dissolved in water (25 mL) and cooled in an ice bath. Bromine (7.8 g) was added dropwise to give a solution of NaOBr. 1-(4′-Fluoro-biphenyl-4-yl)-ethanone (0.01 mol) was dissolved in dioxane (35 mL) and warmed to 50° C. in a water bath. The NaOBr solution was added slowly to the stirred solution of the biphenyl acetate and stirring continued at 50° C. for a further 20 minutes. The solution was allowed to cool and a solution of sodium metabisulphite (8 g in 40 mL water) was added followed by water (170 mL). 50 mL of the liquid was evaporated under reduced pressure with heating. The remainder was acidified with HCl (5 mL) and a white precipitate formed upon cooling. The precipitate was filtered and recrystallised from acetic acid to give the title compound. δC (CDCl3, 62.9 MHz): 115.9, 126.8, 129.2, 129.6, 129.8 (d, J 2.9), 135.5 (d, J 2.9), 143.2, 162.4 (d, J 245.1) and 167.2.

Workup

  1. temperatureto cool
  2. custom50 mL of the liquid was evaporated under reduced pressure
  3. temperaturewith heating
  4. customa white precipitate formed
  5. temperatureupon cooling
  6. filtrationThe precipitate was filtered
  7. customrecrystallised from acetic acid

Sources & evidence

ORD record
ord-f4e8cebf7e8249d6b95b7196fbd0c0bd
Source dataset
uspto-grants-2009_08
Patent number
US07572825B2

Linked notes

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