Hydrochloric Acid → 2-Fluoro-4-phenylbenzoic acid

HRID 2053711Notes

Reaction equation

HRID 2053711 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10]C)=[O:9].[OH-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69129634Methyl 2-fluoro-4-phenylbenzoate

Product 1

HCID 113902902-Fluoro-4-phenylbenzoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Combine methyl 3-fluorobiphenyl-4-carboxylate (8.18 g, 35.5 mmol), THF (225 mL), and 1.0 M aqueous sodium hydroxide (225 mL). Heat at 50° C. for 8 h. Cool to room temperature, add 1.0 M aqueous hydrochloric acid (300 mL), and extract with 2×200 mL ethyl acetate. Separate the organic phase, dry over MgSO4, filter, and evaporate in vacuo to afford 7.12 g (93%) of 3-fluorobiphenyl-4-carboxylic acid as a white solid. 1H NMR (d6-DMSO, 300 MHz) 13.22 (br s, 1H), 7.93 (t, J=8.1 Hz, 1H), 7.74-7.78 (m, 2H), 7.60-7.66 (m, 2H), 7.40-7.52 (m, 3H); IR (cm−1, KBr): 3035, 2666, 2575, 1699, 1621, 1563, 1408, 1298, 1265, 1193, 904; Anal calc'd for C13H9FO2: C 72.22, H 4.20; Found: C 72.18, H 4.35.

Workup

  1. temperatureCool to room temperature
  2. extractionextract with 2×200 mL ethyl acetate
  3. customSeparate the organic phase
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo

Sources & evidence

ORD record
ord-2d863e34e9804b3e8eb50f852e513413
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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