1,3-Dibromopropane → methyl 8-chloro-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylate

HRID 1271581노트

반응식

HRID 1271581 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Br[CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>CC(=O)C>[Cl:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]2[O:12][CH2:17][CH2:16][CH2:15][O:13][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 18613685Methyl 5-chloro-2,3-dihydroxybenzoate

생성물 1

HCID 18613659methyl 8-chloro-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylate수율 94.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of intermediate (9) (0.3 mol), 1,3-dibromopropane (0.42 mol) and K2CO3 (0.66 mol) in 2-propanone (500 ml) was stirred and refluxed for 20 hours, then filtered hot and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent:DCM). The desired fractions were collected and the solvent was evaporated. Toluene was added and azeotroped on the rotary evaporator, yielding 69 g of methyl 8-chloro-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylate (intermediate 10).

후처리

  1. temperaturerefluxed for 20 hours
  2. filtrationfiltered hot
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent:DCM)
  5. customThe desired fractions were collected
  6. customthe solvent was evaporated
  7. additionToluene was added
  8. customazeotroped on the rotary evaporator

출처 및 근거

ORD 기록
ord-15b7e2df439f499c9a22f43339419139
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205410B2

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