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

HRID 272731노트

반응식

HRID 272731 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-90ea855f191c478280631464e293b6bd
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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