Triethylamine → 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid

HRID 2186451Notes

Reaction equation

HRID 2186451 reaction equation
C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.Br[C:38]1[C:46]2[O:45][C:44]([CH2:47][CH3:48])=[N:43][C:42]=2[C:41]([O:49][CH:50]([F:52])[F:51])=[CH:40][CH:39]=1.[C]=[O:54].C1[CH2:59][O:58]CC1.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:51][CH:50]([F:52])[O:49][C:41]1[C:42]2[N:43]=[C:44]([CH2:47][CH3:48])[O:45][C:46]=2[C:38]([C:59]([OH:58])=[O:54])=[CH:39][CH:40]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 21881883Oxolane--water (1/1)HCID 22456638HCID 22456638, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 224566434-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Palladium(II) acetate (54 mg), 1,3-bis(diphenylphosphino)propane (198 mg) and triethylamine (3.3 ml) were added to a solution of 7-bromo-4-difluoromethoxy-2-ethylbezooxazole (0.7 g) in THF/water (30 ml/15 ml). The mixture was heated at 90° C. under 100 psi of carbon monoxide for 4 days. The reaction mixture was allowed to cool to room temperature and the pressure released. The THF was removed in vacuo and the residue diluted with water (10 ml) and washed with ethyl acetate (50 ml). The aqueous layer was acidified to pH 3 with 2N hydrochloric acid and extracted with ethyl acetate (150 ml). Separation of the organic layer, drying over magnesium sulphate, filtering and removal of the solvent in vacuo afforded the title compound as an off-white solid (0.47 g).

Workup

  1. customThe THF was removed in vacuo
  2. additionthe residue diluted with water (10 ml)
  3. washwashed with ethyl acetate (50 ml)
  4. extractionextracted with ethyl acetate (150 ml)
  5. customSeparation of the organic layer
  6. dry with materialdrying over magnesium sulphate
  7. filtrationfiltering
  8. customremoval of the solvent in vacuo

Sources & evidence

ORD record
ord-9b1b8aecb630487f9ef4a2915e3c9c22
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

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