Benzoyl Peroxide → Dimethyl 4-(bromomethyl)isophthalate

HRID 1685393

반응식

HRID 1685393 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>ClCCl.CC(=O)OCC>[Br:16][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

참가 물질

7

반응물 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 899711,3-Benzenedicarboxylic acid, 4-methyl-, 1,3-dimethyl ester2회HCID 516892Sodium Bicarbonate

생성물 1

HCID 14920817Dimethyl 4-(bromomethyl)isophthalate수율 72.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of dimethyl 4-methylisophthlate (Chemical Formula 4) (4 g, 19.2 mmol) in distilled dichloromethane were added N-bromosuccinimide (NBS, 4.8 g, 26.9 mmol) and benzoic peroxyanhydride (0.47 g, 19.2 mmol), followed by reaction at 80° C. for 24 hours in a pressure vessel with constant stirring. The reaction progress was monitored by TLC [Hex:EA=3:1]. When the reaction was detected to have reached completion, saturated NaHCO3 was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer thus formed was dried over anhydrous MgSO4, filtered and concentrated in a vacuum. The purification of the concentrate through column chromatography [Hexane: EtOAc=20:1] produced 4 g of dimethyl 4-(bromomethyl)isophthalate (Chemical Formula 5) (70%).

후처리

  1. customfollowed by reaction at 80° C. for 24 hours in a pressure vessel with constant stirring
  2. additionwas added to the reaction mixture
  3. extractionfollowed by extraction with dichloromethane
  4. customThe organic layer thus formed
  5. dry with materialwas dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in a vacuum
  8. customThe purification of the
  9. concentrationconcentrate through column chromatography [Hexane: EtOAc=20:1]

출처 및 근거

ORD 기록
ord-3aeca7e6f54f45658f5315fd3ee41353
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148402B2

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