4-Toluenesulfonyl chloride → 2-Cyanomethyl-5-fluoro-4-methoxy-benzoic acid

HRID 2100726Notes

Reaction equation

HRID 2100726 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[N:12]O)[C:8]2=[O:11])=[CH:4][C:3]=1[O:14][CH3:15].[OH-].[Na+].C1(C)C=CC(S(Cl)(=O)=[O:25])=CC=1>>[C:7]([CH2:6][C:5]1[CH:4]=[C:3]([O:14][CH3:15])[C:2]([F:1])=[CH:10][C:9]=1[C:8]([OH:11])=[O:25])#[N:12]

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 766087786-Fluoro-5-methoxy-indan-1,2-dione 2-oxime

Product 1

HCID 577998772-Cyanomethyl-5-fluoro-4-methoxy-benzoic acidYield 90%

Conditions

Temperature
50 °C

Procedure

6-Fluoro-5-methoxy-indan-1,2-dione 2-oxime (3.9 g) was added to a solution of 36.4 ml 8% NaOH, and the mixture was heated to 50° C. Then p-Toluenesulfonyl chloride (4.62 g) was added in portions to the mixture, and the mixture was heated at 80° C. for 15 min. After cooled to room temperature, the precipitate was removed from the mixture. The filtrate was acidified with concentrated HCl to PH=3-4 and the precipitate was collected and dried to give product as colorless solid (3.5 g, 90% yield). LC-MS: m/e 208 (M−1)

Workup

  1. temperaturethe mixture was heated at 80° C. for 15 min
  2. temperatureAfter cooled to room temperature
  3. customthe precipitate was removed from the mixture
  4. customthe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-b7259ba02f5f4f1b9ea6abd0d19d14e0
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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