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

HRID 272731Notes

Reaction equation

HRID 272731 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-90ea855f191c478280631464e293b6bd
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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