Carbon tetrabromide → 4-(Bromomethyl)-2,2-dimethyloxolane

HRID 709801Notes

Reaction equation

HRID 709801 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH2:5][CH:4]([CH2:7]O)[CH2:3]1.C(Br)(Br)(Br)[Br:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:11][CH2:7][CH:4]1[CH2:5][O:6][C:2]([CH3:9])([CH3:1])[CH2:3]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15365931Tetrahydro-5,5-dimethyl-3-furanmethanol

Product 1

HCID 1177602254-(Bromomethyl)-2,2-dimethyloxolaneYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5,5-dimethyltetrahydrofuran-3-yl)methanol (2.00 g) in dichloromethane (30 ml) were added carbon tetrabromide (6.10 g) and triphenylphosphine (4.80 g) at room temperature. The reaction mixture was stirred at room temperature for 20 hr, and extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.40 g) as a colorless oil.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-c1a3e6f38bad41f88a2418f397c49d7b
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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