Sodium Sulfite → 5-amino-4-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one

HRID 1850378ノート

反応式

HRID 1850378 の反応式
[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]

参加物

5

反応物 3

HCID 24437Sodium SulfiteHCID 231141353(2H)-Benzofuranone, 5-amino-2,2,6,7-tetramethyl-HCID 23500184Tetra-n-butylammonium tribromide

生成物 1

HCID 667597955-amino-4-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one収率 72.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  1. customsynthesized in Reference Example 20 at 0° C.
  2. extractionextraction
  3. customThe extract was dried
  4. customAfter that, the solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 98:2 to 85:15)

出典と根拠

ORDレコード
ord-b18b6ddd688442f09fe6a12eec2f3e05
出典データセット
uspto-grants-2015_02
特許番号
US08957069B2

反応ノート

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