Bromoform → 4-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxolane

HRID 272731ノート

反応式

HRID 272731 の反応式
[CH3:1][C:2]1([CH3:10])[O:6][CH:5]([CH2:7][CH2:8]O)[CH2:4][O:3]1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)Br>ClCCl>[Br:12][CH2:8][CH2:7][CH:5]1[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]1

参加物

6

反応物 4

HCID 5558BromoformHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 42197542-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

生成物 1

HCID 133630354-(2-Bromoethyl)-2,2-dimethyl-1,3-dioxolane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (292 mg, 2 mmol) in dichloromethane (20 mL) at 0° C. was added carbon tetrabromide (796 mg, 2.4 mmol) and polymer-supported triphenyl phosphine (1 g, 3 mmol). After stirring for 1.75 hours and slowly warming to room temperature, the reaction mixture was filtered through Celite and rinsed with additional dichloromethane. The filtrate was concentrated to give the product as a mixture of product and bromoform (2:1). MS (DCI) m/e 208 (M+NH4—H2O)+; 1H NMR (300 MHz, DMSO-d6) □ 4.15 (m, 1H), 4.02 (dd, J=8.1, 6.1 Hz, 1H), 3.47-3.62 (m, 3H), 1.94-2.09 (m, 2H), 1.32 (s, 3H), 1.26 (s, 3H).

後処理

  1. filtrationthe reaction mixture was filtered through Celite
  2. washrinsed with additional dichloromethane
  3. concentrationThe filtrate was concentrated
  4. customto give the product

出典と根拠

ORDレコード
ord-90ea855f191c478280631464e293b6bd
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

反応ノート

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