Triphenylphosphine → Ethyl 12-bromododecanoate

HRID 2410623ノート

反応式

HRID 2410623 の反応式
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:44])C(=O)C1>ClCCl>[Br:44][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 15635900Ethyl 12-hydroxydodecanoate

生成物 1

HCID 19002561Ethyl 12-bromododecanoate収率 93.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 100 mL two-neck flask with a reflux condenser and magnetic anchor, under a static head of nitrogen, ethyl 12-hydroxydodecanoate (1.65 g, 6.7 mmol) is dissolved in dichloromethane (20 mL). PPh3 (1.93 g, 7.4 mmol) and NBS (1.6 g, 7.0 mmol) are added. The mixture is left stirring under reflux conditions for 24 hours. It is concentrated in the Rotavapor and the product is purified with column chromatography on silica gel with an eluant mixture of petroleum ether/ethyl acetate 5/1. 1.92 g (yield=92%) of ethyl 12-bromododecanoate are isolated as a light yellowish oil.

後処理

  1. waitThe mixture is left
  2. concentrationIt is concentrated in the Rotavapor
  3. customthe product is purified with column chromatography on silica gel with an eluant mixture of petroleum ether/ethyl acetate 5/1

出典と根拠

ORDレコード
ord-271eb0aa7ce245d880310010a5dcac8f
出典データセット
uspto-grants-2014_08
特許番号
US08816107B2

反応ノート

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