Hydrogen Bromide → HCID 66759870, compound

HRID 1850394Notes

Reaction equation

HRID 1850394 reaction equation
C[O:2][C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[C:8](=[O:14])[C:7]=2[C:6]([CH3:15])=[CH:5][C:4]=1[CH3:16].Br.O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[OH:2][C:3]1[C:11]2[O:10][C:9]([CH3:12])([CH3:13])[C:8](=[O:14])[C:7]=2[C:6]([CH3:15])=[CH:5][C:4]=1[CH3:16]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 66760811HCID 66760811, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66759870HCID 66759870, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-methoxy-2,2,4,6-tetramethyl-1-benzofuran-3(2H)-one (1.10 g, 4.99 mmol) synthesized in Reference Example 68, 48% hydrobromic acid (20 mL) and acetic acid (4 mL) was stirred at 100° C. for 15 hours. The reaction solution was poured into cold saturated sodium bicarbonate water in ice bath and extracted using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5 to 80/20) to give 980 mg of the title compound (yield: 95%).

Workup

  1. extractionextracted
  2. washThe extract was washed with saturated saline
  3. customdried
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5 to 80/20)

Sources & evidence

ORD record
ord-bb2f94f799fa4254a3f38b11f704b804
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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