4-Cyano-3-fluorobenzoic acid → HCID 68453663, compound

HRID 2355275Notes

Reaction equation

HRID 2355275 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[F:18])#[N:8]>O1CCCC1>[NH2:8][CH2:7][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[F:18]

Participants

4

Reactant 2

HCID 27784684-Cyano-3-fluorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 68453663HCID 68453663, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

Add 1M lithium aluminum hydride in tetrahydrofuran (121 mL, 121 mmol) to anhydrous tetrahydrofuran (100 mL) under argon gas. Warm the reaction mixture to 40° C. and add in small portions 4-cyano-3-fluorobenzoic acid (5.0 g, 30.28 mmol) over a 1 hr period. Stir the reaction mixture at 40° C. for 4 hrs and then at room temperature overnight. Cool the reaction mixture to 0° C. and quench by the sequential addition of water (5 mL), 15% sodium hydroxide solution (17 mL), and water (5 mL). Allow the mixture to warm-up to room temperature and stir for 1 hr. Filter the precipitate through diatomaceous earth and concentrate the filtrate to provide the title compound (4.4 g, 28.4 mmol).

Workup

  1. customat room temperature
  2. customovernight
  3. temperatureCool the reaction mixture to 0° C.
  4. customquench by the sequential addition of water (5 mL), 15% sodium hydroxide solution (17 mL), and water (5 mL)
  5. temperatureAllow the mixture to warm-up to room temperature
  6. stirringstir for 1 hr
  7. filtrationFilter the precipitate through diatomaceous earth
  8. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-0ad20c798cd9422b87ee5675c7cff5b5
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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