Benzoyl Peroxide → Methyl 4-(bromomethyl)-2-methylbenzoate

HRID 1633113

반응식

HRID 1633113 반응식
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CC1C=CC=C2C=1COC2=O>C(Cl)(Cl)(Cl)Cl>[C:12]([C:11]1[CH:16]=[CH:17][C:18]([CH2:20][Br:1])=[CH:19][C:10]=1[CH3:9])([O:14][CH3:15])=[O:13]

참가 물질

6

반응물 4

HCID 7187Benzoyl PeroxideHCID 32031Methyl 2,4-dimethylbenzoateHCID 67184N-bromobutanimideHCID 6387554-methyl-2-benzofuran-1(3H)-one

생성물 1

HCID 19372658Methyl 4-(bromomethyl)-2-methylbenzoate

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

N-Bromosuccinimide (44.9 g) was added to a solution of methyl 2,4-dimethylbenzoate (41.36 g) in carbon tetrachloride containing a trace of dibenzoyl peroxide. The mixture was heated under reflux until no orange colour persisted then cooled, filtered and the filtrate evaporated to leave an oil. This was distilled until ~16 g distillate bp 98°-140°/0.8-5 mm (starting material) had been collected. The residue was then heated at atmospheric pressure until no more methyl bromide was evolved, to give a mixture of the title compound and 4-methylphthalide. Addition of hot petrol and filtration from the phthalide gave after evaporation the title compound. τ(CDCl3) 7.48 (3H, s), 6.21 (3H, s), 5.65 (2H, s), 2.6-2.93 (2H, m), 2.18 (1H, d, J=8 Hz).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux until no orange colour
  3. temperaturepersisted then cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customto leave an oil
  7. distillationThis was distilled until ~16 g distillate bp 98°-140°/0.8-5 mm (starting material)
  8. customhad been collected
  9. temperatureThe residue was then heated at atmospheric pressure until no more methyl bromide
  10. customto give

출처 및 근거

ORD 기록
ord-347060000d0f4dfaac196fc98fd05664
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04478849

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