(6,7-Difluoro-3-methyl-1,2-benzisoxazol-5-yl)methanol → HCID 86658113, compound

HRID 577968Notes

Reaction equation

HRID 577968 reaction equation
[F:1][C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[C:3]=1[F:14]>C(Cl)Cl.[O-2].[O-2].[Mn+4].O=[Mn]=O>[F:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[C:3]=1[F:14]

Participants

5

Reactant 1

HCID 67356869(6,7-Difluoro-3-methyl-1,2-benzisoxazol-5-yl)methanol2×

Product 1

HCID 86658113HCID 86658113, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (6,7-difluoro-3-methyl-1,2-benzisoxazol-5-yl)methanol (Intermediate 334, 0.7 g, 3.51 mmol) and manganese dioxide (6.11 g, 70.30 mmol) in CH2Cl2 (70 ml) was stirred at room temperature for 3 days. TLC shows conversion to a higher Rf spot with starting material. Additional MnO2 (5 g) was added and the mixture was heated to reflux for 24 hours. The mixture was filtered through celite and rinsed well with CH2Cl2. Solvent was removed from the filtrate to give 640 mg of product as a tan solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 hours
  3. filtrationThe mixture was filtered through celite
  4. washrinsed well with CH2Cl2
  5. customSolvent was removed from the filtrate

Sources & evidence

ORD record
ord-0745c48a18e8433fa518a26b6d0b307c
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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