Imidazole → 8-bromo-1,4-dioxaspiro[4.5]decane

HRID 555844Notes

Reaction equation

HRID 555844 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[O:30]1[C:34]2([CH2:39][CH2:38]C(O)[CH2:36][CH2:35]2)[O:33][CH2:32][CH2:31]1>C(Cl)Cl>[Br:5][CH:1]1[CH2:38][CH2:39][C:34]2([O:33][CH2:32][CH2:31][O:30]2)[CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 137651298-bromo-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (11.0 g, 33.2 mmol) was added to a solution of triphenylphosphine (8.70 g, 33.2 mmol), imidazole (2.47 g, 36.3 mmol), and 1,4-dioxaspiro[4.5]decan-8-ol (5.0 g, 31.6 mmol) in DCM (150 mL) under argon at 0° C. The ice bath was removed and the mixture was stirred for 24 h at RT. The solvent was removed in vacuo to give an oil that was purified by silica gel chromatography to give 8-Bromo-1,4-dioxaspiro[4.5]decane.

Workup

  1. customThe ice bath was removed
  2. customThe solvent was removed in vacuo
  3. customto give an oil that
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-822dba7c7ae043a3ba453c5f51f89d51
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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