4-Hydroxybenzoic Acid → HCID 28604971, compound

HRID 1500972Notes

Reaction equation

HRID 1500972 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.F[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[C:14]([C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=1[O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)#[N:15]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 28604971HCID 28604971, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-hydroxybenzoic acid (7 g, 50 mmol) and 2-fluorobenzonitrile (7.36 g, 60 mmol) in dimethylsulfoxide (40 mL) was added potassium carbonate (20 g, 150 mmol). The reaction mixture was stirred at 120° C. for 4 hours. After the reaction, the temperature was allowed to cool to room temperature, then the mixture was poured into ice water (100 mL). The mixture was neutralized to pH=3 with concentrated hydrochloric acid and then extracted with ethyl acetate (15 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to give 4-(2-cyanophenoxy)benzoic acid as a white solid (5.80 g, 48.5%). LRMS (M+H)− m/z: calcd 239.06. found 239. 1H NMR (300 MHz, d6-DMSO): δ 12.94 (s, 1H), 7.99-7.91 (m, 3H), 7.71 (t, J=8.4 Hz, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.17-7.14 (m, 3H).

Workup

  1. customAfter the reaction
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate (15 mL×3)
  4. dry with materialThe combined organic phase was dried by sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-13418a7086324b6c9f7a84ff172d480a
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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