Carbon tetrabromide → 1,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-

HRID 908526ノート

反応式

HRID 908526 の反応式
[CH3:1][C:2]1([CH3:11])[O:7][CH2:6][CH:5]([CH2:8][CH2:9]O)[CH2:4][O:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:32][CH2:9][CH2:8][CH:5]1[CH2:6][O:7][C:2]([CH3:11])([CH3:1])[O:3][CH2:4]1

参加物

6

反応物 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 118160112-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanol

生成物 1

HCID 1789881,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of compound 32 (84 g, 0.528 mol) in dry DMF (500 mL) was added triphenylphosphine (207 g, 0.79 mol) with vigorous stirring until it becomes a clear solution. The mixture was cooled to 0° C. and added CBr4 (260 g, 0.79 mol) portion wise over a period of 30 min and allowed to stir at RT for 5 h. The reaction mixture was cooled to 0° C., added saturated NaHCO3 solution (200 mL) and extracted with hexane (4×200 mL). The combined organic layer was dried, concentrated under vacuum and the crude title compound (117 g) was used for next reaction without any purification. TLC: Pet. ether/EtOAc, 7:3, Rf=0.6

後処理

  1. stirringto stir at RT for 5 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with hexane (4×200 mL)
  4. customThe combined organic layer was dried
  5. concentrationconcentrated under vacuum
  6. customthe crude title compound (117 g) was used for next reaction without any purification

出典と根拠

ORDレコード
ord-8a9400e2ee204391b432642c46834d37
出典データセット
uspto-grants-2011_09
特許番号
US08017620B2

反応ノート

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