Diethylamine → 3-Bromo-4-(1-octynyl)thiophene

HRID 1686168ノート

反応式

HRID 1686168 の反応式
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][CH:3]=1.C(NCC)C.[CH:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:7][C:6]1[C:2]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:3][S:4][CH:5]=1

参加物

6

反応物 3

HCID 8021DiethylamineHCID 123701-OctyneHCID 184523,4-Dibromothiophene

生成物 1

HCID 201471773-Bromo-4-(1-octynyl)thiophene収率 25.7%

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 83717Copper iodide触媒

反応条件

温度
60 °C

実験手順

Into a 250 mL 4 necked RB flask equipped with a magnetic stirring bar, thermometer, rubber septum, argon inlet and reflux condenser with argon outlet (tubed to a silicon oil bubbler) is added 59.4 g (246 mmol) of 3,4-dibromothiophene, 44.0 g of diethylamine, 27.0 g (245 mmol) of 1-octyne, 148 mg of triphenylphosphine, 106 mg of copper iodide and 295 mg dichlorobis(triphenylphosphine) palladium(II). The mixture is heated with a silicon oil bath to 60° C. under argon with stirring for 40 hrs. The cooled mixture is then concentrated on a rotary evaporator at reduced pressure and the residue taken up in 200 mL of pentane and washed with 2×25 mL of water and the pentane phase dried over sodium sulfate and then concentrated on a rotary evaporator. The residue is then distilled at 55-60 ° C. and 0.40 torr to remove 2.3 g of unreacted 3,4-dibromothiophene. The residue was chromatographed through silica gel eluting with hexanes to yield 17.1 g of 3-bromo-4(oct-1-ynyl)thiophene as a light yellow-orange oil which was used directly to prepare 2-hexylselenolo[2,3-c]thiophene.

後処理

  1. temperaturethermometer, rubber septum, argon inlet and reflux condenser with argon outlet (
  2. concentrationThe cooled mixture is then concentrated on a rotary evaporator at reduced pressure
  3. washwashed with 2×25 mL of water
  4. dry with materialthe pentane phase dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. distillationThe residue is then distilled at 55-60 ° C.
  7. custom0.40 torr to remove 2.3 g of unreacted 3,4-dibromothiophene
  8. customThe residue was chromatographed through silica gel eluting with hexanes

出典と根拠

ORDレコード
ord-c1238e2c7f714bec9bde979572c76761
出典データセット
uspto-grants-2012_04
特許番号
US08148548B2

反応ノート

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