m-Chloroperbenzoic acid → HCID 54419155, compound

HRID 892526Notes

Reaction equation

HRID 892526 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:11])([CH3:12])[CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=3[O-:28])[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895628HCID 19895628, compound

Product 1

HCID 54419155HCID 54419155, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

330 mg of 6-bromo-3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran were dissolved in 10 ml of dichloromethane at room temperature and 280 mg of m-chloroperbenzoic acid were added. After stirring at room temperature for 3 days the mixture was washed with sodium bisulphite solution, then with sodium bicarbonate solution and finally with water. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 4% (v/v) methanol/ethyl acetate for the elution to give 250 mg of 2-(6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide as a foam. NMR (300 MHz, CDCl3): 8.35-8.30 (1H, m), 7.26-7.15 (3H, m), 7.13-7.05 (1H, m), 6.95 (1H, broad s), 6.75 (1H, d, 9Hz), 5.28 (1H, broad s), 2.42 (1H, dd, 13Hz, 6Hz), 1.7 (1H, broad s), 1.42 (3H, s), 1.37 (3H, s). MS (EI): 335 (M+ [Br81 ], 333 (H+ [Br79 ]), 318 (M+ [Br81 ]-OH), 316 (M+ [Br79 ]-OH)

Workup

  1. washwas washed with sodium bisulphite solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel using 4% (v/v) methanol/ethyl acetate for the elution

Sources & evidence

ORD record
ord-b652a75e5f36413dafa15fb874a36a23
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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