N-bromobutanimide → HCID 69522120, compound

HRID 460302Notes

Reaction equation

HRID 460302 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]=2[CH:16]=1)(=[O:5])=[O:4].[Br:17]N1C(=O)CCC1=O>FC(F)(F)C(O)=O.S(=O)(=O)(O)O>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[C:8]([Br:17])[C:9]2[O:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]=2[CH:16]=1)(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 69521413HCID 69521413, compound

Product 1

HCID 69522120HCID 69522120, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3,3-dimethyl-2,3-dihydro-benzofuran-5-sulfonic acid methylamide (215 mg, 0.89 mmol) in trifluoroacetic acid (5 mL) and sulfuric acid (1 mL) was added portionwise N-bromosuccinimide (317 mg, 1.78 mmol). The mixture was stirred at room temperature overnight, poured into a solution of ice-water and rinsed with dichloromethane. The layers were separated. The aqueous layer was extracted twice with dichloromethane and the organic combined extract was washed with water, an aqueous solution of sodium bicarbonate, brine, dried (MgSO4), filtered and evaporated. The residue was chromatographed on silica gel (30% ethyl acetate in hexane) to afford 91 mg of 7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-sulfonic acid methylamide. 32% yield. 1H-NMR (300 MHz, CDCl3): 1.40 (s, 6H), 2.68 (d, J=5.3 Hz, 3H), 4.21 (m, 1H), 4.45 (s, 2H), 7.52 (d, J=1.8 Hz, 1H), 7.83 (d, J=1.8 Hz, 1H).

Workup

  1. washrinsed with dichloromethane
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted twice with dichloromethane
  4. extractionthe organic combined extract
  5. washwas washed with water
  6. dry with materialan aqueous solution of sodium bicarbonate, brine, dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5133a47a94644d6c8f2f1b160f9cb92b
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

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