Methanol → 5-(tert-Butyl)-7-fluoro-3-methoxyisobenzofuran-1(3H)-one

HRID 407605Notes

Reaction equation

HRID 407605 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[O:13]CC(C)(C)N=2)=[C:7]([CH:19]2[O:24][CH2:23]CC[O:20]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.S(=O)(=O)(O)O>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[C:9]([F:11])[CH:10]=1)[C:12](=[O:13])[O:20][CH:19]2[O:24][CH3:23])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 594737622-(4-Tert-butyl-2-1,3-dioxinan-2-yl-6-fluoro-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole

Product 1

HCID 866839105-(tert-Butyl)-7-fluoro-3-methoxyisobenzofuran-1(3H)-oneYield 87.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 101f (68.8 g, 205.4 mmol), methanol (1340 mL) and 50% aqueous sulfuric acid (881 mL) was stirred at reflux overnight. The reaction mixture was poured into 400 mL of water, extracted with DCM (3×1000 mL). The combined organic extracts were washed with 400 mL of brine, dried over Na2SO4, filtered and concentrated to dry to provide 101g (43 g) as a off-white solid which was used in the next step without further purification LCMS (ESI) m/z 225 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with DCM (3×1000 mL)
  3. washThe combined organic extracts were washed with 400 mL of brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto dry

Sources & evidence

ORD record
ord-ba4de18737d240dfaa1929508c3d32cf
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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