Ozone → HCID 58197315, compound

HRID 1503398Notes

Reaction equation

HRID 1503398 reaction equation
[O:1]=[O+][O-].[CH2:4]([C:7]1[C:15]([F:16])=[C:14]([F:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])[CH:5]=C.[BH4-].[Na+]>C(Cl)Cl>[F:16][C:15]1[C:7]([CH2:4][CH2:5][OH:1])=[C:8]([CH:12]=[CH:13][C:14]=1[F:17])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 58197886HCID 58197886, compound

Product 1

HCID 58197315HCID 58197315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A steam of O3 was bubbled through a solution of 2-allyl-3,4-difluorobenzoic acid (13 g, 0.065 mol) in absolute CH2Cl2 (200 mL) at −78° C. until the mixture was turned blue. Then NaBH4 (7.25 g, 0.196 mol) in was added to the above mixture, and the final mixture was stirred at room temperature overnight. The solution was concentrated. Water was added at 0° C., and the mixture was acidified by adding 6 N HCl, and was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give 3,4-difluoro-2-(2-hydroxyethyl)benzoic acid (8.2 g, crude).

Workup

  1. concentrationThe solution was concentrated
  2. additionWater was added at 0° C.
  3. additionby adding 6 N HCl
  4. extractionwas extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f5ac25e8db684533b4da53d4f3175f1b
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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