1,10-Dibromodecane → 1-Bromohexadec-1-yne

HRID 1589578노트

반응식

HRID 1589578 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12].[C:13]([Li])#[C:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1COCC1.CN(P(N(C)C)N(C)C)C>[C:11]([Br:12])#[C:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

5

반응물 2

HCID 2214831,10-DibromodecaneHCID 178506798HCID 178506798, 화합물

생성물 1

HCID 198481531-Bromohexadec-1-yne수율 34.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15355Hexamethylphosphorous triamide용매

실험 절차

A 3 liter, 2-necked round bottom flask was equipped with a magnetic stir bar, an inlet valve and a septum. After being purged with an argon atmosphere, the flask was charged with 615 g (2.1 mol) of 1,10-dibromodecane in 350 mL of THF and 125 mL of hexamethylphosphorus triamide. A solution containing about 1 mol of hexynyllithium, prepared as described above, was then added to the solution of dibromide via the septum. The reaction mixture was allowed to stir overnight, then quenched by pouring over about 1 L of water. The reaction mixture was diluted with about 500 mL of hexane, phases separated and the organic layer washed twice with 500 mL aliquots of water. The organic layer was then dried over MgSO4, filtered, solvent stripped on the rotary evaporator, then vacuum distilled through a 2 foot column packed with 1/4" glass helices. About 104 g (35 mol % yield) of hexadecynyl bromide was obtained with a boiling point of 135° C. @ 0.3 mm Hg.

후처리

  1. customA 3 liter, 2-necked round bottom flask was equipped with a magnetic stir bar, an inlet valve
  2. customAfter being purged with an argon atmosphere
  3. customprepared
  4. customquenched
  5. additionby pouring over about 1 L of water
  6. additionThe reaction mixture was diluted with about 500 mL of hexane, phases
  7. customseparated
  8. washthe organic layer washed twice with 500 mL aliquots of water
  9. dry with materialThe organic layer was then dried over MgSO4
  10. filtrationfiltered
  11. customsolvent stripped on the rotary evaporator
  12. distillationvacuum distilled through a 2 foot column

출처 및 근거

ORD 기록
ord-73fa0fa4cdd8409fa7f095f4391a981d
출처 데이터셋
uspto-grants-1986_02
특허 번호
US04571438

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