N-bromobutanimide → 2-[4-(Bromomethyl)phenyl]-2-phenyl-1,3-dioxolane

HRID 1406677Notes

Reaction equation

HRID 1406677 reaction equation
[C:1]1([C:7]2([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[O:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:19]N1C(=O)CCC1=O>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:8][CH2:9][CH2:10][O:11]2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 18715593HCID 18715593, compound

Product 1

HCID 572491342-[4-(Bromomethyl)phenyl]-2-phenyl-1,3-dioxolaneYield 55%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a round-bottom flask were added 12 (3.54 g, 14.7 mmol, 1.0 equiv.), N-bromosuccinimide (2.9 g, 16.2 mmol, 1.1 equiv.), AIBN (48 mg, 0.29 mmol, 0.02 equiv.), and CCl4 (60 mL, 0.25 M). The reaction mixture was stirred at reflux for 6.5 hours. The reaction mixture was cooled to room temperature. The succinimide was filtered and washed with CC14. The filtrate was concentrated and crystallized from EtOAc/hexanes to yield 13 (2.57 g, 55%) as a white solid. 1H-NMR (500 MHz, CDCl3) δ 7.56-7.53 (m, 4H), 7.38-7.35 (m, 4H), 7.33-7.29 (m, 1H), 4.48 (s, 2H), 4.08 (s, 4H). 13C-NMR (125 MHz, CDCl3): δ 142.4, 141.8, 137.4, 128.8, 128.1, 128.1, 126.5, 125.9, 109.0, 64.8, 33.1.

Workup

  1. temperatureat reflux for 6.5 hours
  2. filtrationThe succinimide was filtered
  3. washwashed with CC14
  4. concentrationThe filtrate was concentrated
  5. customcrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-746210664ca940d8a76bfca26997eb50
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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