2,3-Dibromopropene → 7-[(2-bromoallyl)oxy]-4-methyl-2H-chromen-2-one

HRID 225032

반응식

HRID 225032 반응식
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[O:5][C:4](=[O:13])[CH:3]=1.[Br:14][C:15]([CH2:17]Br)=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:17][C:15]([Br:14])=[CH2:16])=[CH:9][CH:10]=2)[O:5][C:4](=[O:13])[CH:3]=1

참가 물질

5

반응물 3

HCID 105522,3-DibromopropeneHCID 11430Potassium CarbonateHCID 52805674-Methylumbelliferone

생성물 1

HCID 3424497-[(2-bromoallyl)oxy]-4-methyl-2H-chromen-2-one수율 89%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

4-Methyl-7-hydroxycoumarin (2.00 g., 11.4 m mole) was refluxed with freshly-distilled 2,3-dibromopropene (2.72 g., 13.6 m mole), anhydrous potassium carbonate (3.15 g., 22.8 m mole), and acetone (80 ml.) for four hours. The reaction mixture was treated as described for the preparation of Example I, Part 1-A to obtain 4-methyl-7-(2'-bromoallyloxy) coumarin as an off-white solid (3.70 g.) that contained some excess 2,3-dibromopropene. Recrystallization of a portion (500 mg.) from ligroin (b.p. 100°-120° C.) gave needles (394 mg., 89% yield) of m.p. 109.5°-110.5° C. An analytical sample of m.p. 110°-111° C. was obtained by recrystallization from methanol.

후처리

  1. additionThe reaction mixture was treated

출처 및 근거

ORD 기록
ord-119bd61beb0d4d279285b1bd4e15074f
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04235781

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