Sodium Sulfite → 5-amino-4-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one
Reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[NH2:55][C:56]1[C:57]([CH3:69])=[C:58]([CH3:68])[C:59]2[O:63][C:62]([CH3:65])([CH3:64])[C:61](=[O:66])[C:60]=2[CH:67]=1.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[NH2:55][C:56]1[C:57]([CH3:69])=[C:58]([CH3:68])[C:59]2[O:63][C:62]([CH3:64])([CH3:65])[C:61](=[O:66])[C:60]=2[C:67]=1[Br:1]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Tetrabutylammonium tribromide (31.0 g, 64.2 mmol) was added to a tetrahydrofuran solution (200 mL) containing 5-amino-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (6.59 g, 32.1 mmol) synthesized in Reference Example 20 at 0° C., and the mixture was stirred at 0° C. for 2 hours. To the mixture, a saturated sodium sulfite aqueous solution was added, and extraction was performed using ethyl acetate. The extract was dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 98:2 to 85:15) to give 6.60 g of the title compound (yield: 72%).
Workup
- customsynthesized in Reference Example 20 at 0° C.
- extractionextraction
- customThe extract was dried
- customAfter that, the solvent was removed under reduced pressure
- customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 98:2 to 85:15)
Sources & evidence
- ORD record
- ord-b18b6ddd688442f09fe6a12eec2f3e05
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957069B2
Reaction notes
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