Carbon tetrabromide → 1-Undecyne, 11-bromo-

HRID 620552

반응식

HRID 620552 반응식
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[CH:12].C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:14][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[CH:12]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 7601510-Undecyn-1-ol

생성물 1

HCID 1171111-Undecyne, 11-bromo-수율 52.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To an ice-cold solution of 11-hydroxyundecyne (10 g, 59.4 mmoles) in 400 ml of methylene chloride under argon was added in one portion carbon tetrabromide (40.5 g, 0.1224 mole). The reaction mixture was stirred at 0° C. for 5 minutes and triphenylphosphine (29.43 g, 0.1122 mole) was added. The reaction was kept at 0° C. for an additional 15 minutes and stirred at room temperature for 3 hours. The methylene chloride was removed in vacuo. The residue was treated with hexane and the combined organic extract was concentrated in vacuo. The crude product was purified by flash chromatography on silica, eluting with straight hexane, to give 7.2 g (52%) of 11-bromoundecyne as a colorless oil. Following the procedures of Examples 20 and 39(a), a mixture of salicylaldehyde, 11-bromoundecyne and potassium carbonate in dimethylformamide is reacted to furnish 2-(10-undecynyloxy)benzaldehyde.

후처리

  1. waitThe reaction was kept at 0° C. for an additional 15 minutes
  2. stirringstirred at room temperature for 3 hours
  3. customThe methylene chloride was removed in vacuo
  4. additionThe residue was treated with hexane
  5. extractionthe combined organic extract
  6. concentrationwas concentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica
  8. washeluting with straight hexane

출처 및 근거

ORD 기록
ord-292843c0651a46d6aea910a8132274c6
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04820719

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