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

HRID 727191Notes

Reaction equation

HRID 727191 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:13][CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 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 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 17.4 grams (0.11 mole) of 1,4-dioxaspiro[4.5]decan-8-ol (prepared as in Step B of Example 8) and 46.2 grams (0.14 mole) of freshly recrystallized carbon tetrabromide in 100 mL of methylene chloride is cooled to about 0° C., and a solution of 32.3 grams (0.12 mole) of triphenylphosphine in 50 mL of methylene chloride is added dropwise. Upon completion of addition, the reaction mixture is allowed to warm to ambient temperature where it is stirred for about 18 hours. After this time the reaction mixture is concentrated to about one quarter of the original volume. The concentrate is then passed through a pad of silica gel. Elution is accomplished with heptane. The eluate is concentrated under reduced pressure, yielding 8-bromo-1,4-dioxaspiro[4.5]decane.

Workup

  1. additionUpon completion of addition
  2. concentrationAfter this time the reaction mixture is concentrated to about one quarter of the original volume
  3. washElution
  4. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a285140c6de4e9b97765a89407f3a8a
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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