Tetrabutylammonium Fluoride → 7-Bromo-4-(1H-pyrrol-3-yl)-2H-1-benzopyran-2-one

HRID 1901130Notes

Reaction equation

HRID 1901130 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:17]=[CH:16][N:15]([Si](C(C)C)(C(C)C)C(C)C)[CH:14]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[NH:15]1[CH:16]=[CH:17][C:13]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=3)[O:9][C:8](=[O:12])[CH:7]=2)=[CH:14]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23370193HCID 23370193, compound

Product 1

HCID 233702087-Bromo-4-(1H-pyrrol-3-yl)-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the silyl compound from Step 1 (42 mg, 0.094 mmol) in THF (1 mL) was added Bu4NF 1M in THF (94 (L, 0.094 mmol) and the reaction mixture was stirred at r.t. for 15 min. The mixture was diluted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated to give the title compound as an oil.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9f4ea5b90d4e413d8ac8e53754a6f40e
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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