Piperidine → 2-(3,5-Dibromo-4-hydroxyphenyl)-6-hydroxy-3-methyl-4H-1-benzopyran-4-one

HRID 986481

반응식

HRID 986481 반응식
BrBr.[Br:3][C:4]1[CH:5]=[C:6]([CH:20]=[C:21]([Br:24])[C:22]=1[OH:23])[CH:7]1[CH:16]([CH3:17])[C:15](=[O:18])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:19])[CH:13]=2)[O:8]1.CCC(C1C=C(O)C=CC=1O)=O.BrC1C=C(C=C(Br)C=1O)C=O.N1CCCCC1.BrC1(C)C(=O)C2C(=CC=C(O)C=2)OC1C1C=C(Br)C(O)=C(Br)C=1.[OH-].[K+]>C(Cl)(Cl)Cl.O1CCOCC1.C(O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:20]=[C:21]([Br:24])[C:22]=1[OH:23])[C:7]1[O:8][C:9]2[C:14]([C:15](=[O:18])[C:16]=1[CH3:17])=[CH:13][C:12]([OH:19])=[CH:11][CH:10]=2

참가 물질

11

반응물 7

HCID 8082PiperidineHCID 14797Potassium HydroxideHCID 181003,5-Dibromo-4-HydroxybenzaldehydeHCID 24408BromineHCID 703122',5'-DihydroxypropiophenoneHCID 136508183',5'-Dibromo-6,4'-dihydroxy-3-methylflavanoneHCID 212838993,3',5'-Tribromo-6,4'-dihydroxy-3-methylflavanone

생성물 1

HCID 1286002-(3,5-Dibromo-4-hydroxyphenyl)-6-hydroxy-3-methyl-4H-1-benzopyran-4-one

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 6212Chloroform용매HCID 312751,4-Dioxane용매

실험 절차

1.6 g of bromine in 6 ml of chloroform are added dropwise to a solution of 4.12 g of 3',5'-dibromo-6,4'-dihydroxy-3-methylflavanone (m.p. 200°-202°; obtainable by reaction of 2,5-dihydroxypropiophenone with 3,5-dibromo-4-hydroxybenzaldehyde in boiling ethanol in the presence of piperidine) in 55 ml of dioxane while stirring and irradiating (500 watt Agaphot lamp). The mixture is stirred for a further 30 minutes while cooling and irradiating, the usual working-up is carried out, and the resulting crude 3,3',5'-tribromo-6,4'-dihydroxy-3-methylflavanone is dissolved in 100 ml of ethanol. 15 ml of 10% aqueous potassium hydroxide solution are added, and the mixture is boiled for 5 minutes, cooled, poured on to ice and the usual working-up is carried out. 3',5'-Dibrom-6,4'-dihydroxy-3-methylflavone ("D") is obtained, m.p. 264°-265°.

후처리

  1. customirradiating (500 watt Agaphot lamp)
  2. stirringThe mixture is stirred for a further 30 minutes
  3. temperaturewhile cooling
  4. customirradiating
  5. temperaturecooled
  6. additionpoured on to ice

출처 및 근거

ORD 기록
ord-d4c6203d4710429b8fc2774f31ac37aa
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04713465

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