Carbon Dioxide → 3-cyano-2-fluoro-4-methoxybenzoic acid

HRID 2054903Notes

Reaction equation

HRID 2054903 reaction equation
C([N-]C(C)C)(C)C.[Li+].[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:11]=1[C:12]#[N:13].[C:20](=[O:22])=[O:21]>C1COCC1>[C:12]([C:11]1[C:10]([F:9])=[C:17]([CH:16]=[CH:15][C:14]=1[O:18][CH3:19])[C:20]([OH:22])=[O:21])#[N:13]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 5231012-Fluoro-6-methoxybenzonitrileHCID 2724682Lithium diisopropylamide

Product 1

HCID 596566313-cyano-2-fluoro-4-methoxybenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred lithium diisopropylamide solution (1.8M in heptane/THF/ethylbenzene, 44.1 mL, 79.4 mmol) at −50° C. was added a solution of 2-fluoro-6-methoxybenzonitrile (10 g, 66.16 mmol) in THF (80 mL) slowly and stirring was continued at that temperature for 1 h. The reaction mixture was poured onto a stirred slurry of dry ice in dry THF (100 mL). After the mixture had warmed up to room temperature, it was concentrated to about 50 mL, diluted with 6 N HCl (200 mL), extracted with dichloromethane, dried with sodium sulfate, concentrated, and dried in vacuo to give 3-cyano2-fluoro-4-methoxybenzoic acid (12.9 g, 100%).

Workup

  1. concentrationit was concentrated to about 50 mL
  2. additiondiluted with 6 N HCl (200 mL)
  3. extractionextracted with dichloromethane
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-942d16aed93244b4a5a8aac5c64eb9fb
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

Loading…