Carbon tetrabromide → 2-(Bromomethyl)-5,8-dioxaspiro[3.4]octane

HRID 1966815Notes

Reaction equation

HRID 1966815 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]1[C:23]2([O:27][CH2:26][CH2:25][O:24]2)[CH2:22][CH:21]1[CH2:28]O.[Br:30]C(Br)(Br)Br>ClCCl>[Br:30][CH2:28][CH:21]1[CH2:22][C:23]2([O:27][CH2:26][CH2:25][O:24]2)[CH2:20]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 120735835,8-Dioxaspiro[3.4]octane-2-methanol

Product 1

HCID 667332822-(Bromomethyl)-5,8-dioxaspiro[3.4]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (6.28 gm, 24 mmol) in dichloromethane was added drop wise to a solution of 5,8-dioxaspiro[3.4]oct-2-ylmethanol (2.3 gm, 16 mmol) (step d) and tetrabromomethane (6.62 gm, 20 mmol) in dichloromethane. The reaction mixture was stirred at room temperature for about 6 hours. The solvent was removed under reduced pressure and the residue was extracted with diethyl ether. The organic layer was concentrated under reduced pressure to get a crude product, which was purified by column chromatography.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe residue was extracted with diethyl ether
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-27b029d0d56d47e8b60325e2660a95c2
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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