Benzoyl Peroxide → HCID 18421399, compound

HRID 368786Notes

Reaction equation

HRID 368786 reaction equation
[C:1]([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9]([CH3:18])=[C:10]([CH3:17])[C:11](=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C:9]([CH3:18])=[C:10]([CH2:17][Br:19])[C:11](=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 854734225379-14-6

Product 1

HCID 18421399HCID 18421399, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 7-acetoxy-3,4,8-trimethylcoumarin (6.22 g, 25.3 mmol), N-bromosuccinimide (4.61 g, 25.9 mmol) and benzoyl peroxide (30 mg) were refluxed in carbon tetrachloride for 3.5 hours. The mixture was cooled to room temperature and partitioned between CH2Cl2 and water. The organic layer was separated and washed with water several times, then washed with brine. The organic layer was then dried with anhydrous sodium sulfate and evaporated to give crude product (11.8 g) which was recrystallized twice in toluene to give 7-acetoxy-3-bromomethyl-4,8-dimethylcoumarin, a white crystalline solid (4.86 g, 59%). 1H NMR (CDCl3): δ 7.54 (d, J=8.8 Hz, 1H), 7.05 (d, J=8.8 Hz, 1H), 4.57 (s, 2H), 2.50 (s, 3H), 2.37 (s, 3H), 2.28 (s, 3H).

Workup

  1. custompartitioned between CH2Cl2 and water
  2. customThe organic layer was separated
  3. washwashed with water several times
  4. washwashed with brine
  5. dry with materialThe organic layer was then dried with anhydrous sodium sulfate
  6. customevaporated
  7. customto give crude product (11.8 g) which
  8. customwas recrystallized twice in toluene

Sources & evidence

ORD record
ord-c6571f4c906d4a9297a607985cf6eaf9
Source dataset
uspto-grants-2000_10
Patent number
US06133460

Reaction notes

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