Water → 4-(Bromomethyl)-2,2-dimethyloxane

HRID 709807Notes

Reaction equation

HRID 709807 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH:6]([CH2:8]O)[CH2:5][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.O>ClCCl>[Br:12][CH2:8][CH:6]1[CH2:5][CH2:4][O:3][C:2]([CH3:10])([CH3:1])[CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 51072184(2,2-Dimethyloxan-4-yl)methanol

Product 1

HCID 576996994-(Bromomethyl)-2,2-dimethyloxaneYield 30.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2,2-dimethyltetrahydro-2H-pyran-4-yl)methanol (2.50 g) in dichloromethane (30 mL) were added carbon tetrabromide (6.80 g) and triphenylphosphine (5.40 g), and the mixture was stirred at room temperature for 20 hr. Water was added and the mixture was 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 (petroleum ether) to give the title compound (1.10 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted 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 (petroleum ether)

Sources & evidence

ORD record
ord-1a7c6eb60369425cb2328263bba618cd
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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