Benzoyl Peroxide → 4,6-Dibromoisochroman-1-one

HRID 2173150Notes

Reaction equation

HRID 2173150 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH2:6][CH2:5]2.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[C:8](=[O:12])[O:7][CH2:6]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 441308436-bromo-3,4-dihydro-1H-2-benzopyran-1-one

Product 1

HCID 675174614,6-Dibromoisochroman-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

6-Bromo-3,4-dihydro-1H-isochromen-1-one (3.00 g, 13.2 mmol) was dissolved in CCl4 (150 mL) then added N-bromosuccinimide (2.352 g, 13.21 mmol) followed by benzoyl peroxide (0.0960 g, 0.396 mmol) and refluxed for 3 hrs. Filtered and concentrated then chromatographed through a 120 g ISCO Redi-sep. column and eluted with 0-25% ETOAc/Hexane to yield 4,6-dibromo-3,4-dihydro-1H-isochromen-1-one. LC-MS (IE, m/z): 306.9 [M+1]+; 1H-NMR (500 MHz, CDCL3) δ ppm 8.03 (d, J=8.9 Hz, 1H), 7.69 (d, J=7.9 Hz, 1H), 7.68 (s, 1H), 5.32 (t, J=3 Hz, 1H), 4.72-4.81 (q, 1H).

Workup

  1. temperaturerefluxed for 3 hrs
  2. filtrationFiltered
  3. concentrationconcentrated
  4. customthen chromatographed through a 120 g ISCO Redi-sep
  5. washcolumn and eluted with 0-25% ETOAc/Hexane

Sources & evidence

ORD record
ord-ea9187b09cc74bd89c1222431b5e126a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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