Lithium Hydroxide → HCID 86695927, compound

HRID 1398452Notes

Reaction equation

HRID 1398452 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=[CH:10][C:9]=2[F:18])=[C:4]([F:19])[CH:3]=1.[Li+].[OH-]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[CH:10][C:9]=2[F:18])=[C:4]([F:19])[CH:3]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86695924HCID 86695924, compound

Product 1

HCID 86695927HCID 86695927, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of methyl 4-(4-chloro-2-fluorophenyl)-5-fluoronicotinate (600 mg, 2.115 mmol) in tetrahydrofuran (2.5 mL), MeOH (2.5 mL) and water (2.5 mL) was added LiOH (50.7 mg, 2.115 mmol) and the mixture was stirred at rt for 12 h. The volatiles were removed and the residue was diluted with water. The pH was adjusted to 4 with 1.5N HCl. The product was extracted with ethyl acetate (2×5 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford 4-(4-chloro-2-fluorophenyl)-5-fluoronicotinic acid (530 mg, 1.966 mmol, 93% crude yield) the pale brown solid. The material was carried on without further purification. LC/MS (ESI) m/e 269.9 [(M+H)+, calcd for C12H7ClF2NO2 270.0]; LC/MS retention time (method D): tR=0.88 min.

Workup

  1. customThe volatiles were removed
  2. additionthe residue was diluted with water
  3. extractionThe product was extracted with ethyl acetate (2×5 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68d86f3518084c6286f6ba71ddca8030
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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