Benzoyl Peroxide → HCID 18421399, 화합물

HRID 368786노트

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HRID 368786 반응식
[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]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 854734(3,4,8-trimethyl-2-oxochromen-7-yl) acetate

생성물 1

HCID 18421399HCID 18421399, 화합물

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c6571f4c906d4a9297a607985cf6eaf9
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133460

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