Thionyl bromide → HCID 53870913, compound

HRID 1112185Notes

Reaction equation

HRID 1112185 reaction equation
S(Br)([Br:3])=O.[C:5]12(O)[CH2:14][CH:10]([CH2:11][CH2:12][CH2:13]1)[CH:9]1[CH2:15][CH:6]2[CH2:7][CH2:8]1>C1C=CC=CC=1>[Br:3][C:5]12[CH2:14][CH:10]([CH2:11][CH2:12][CH2:13]1)[CH:9]1[CH2:15][CH:6]2[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 13070378HCID 13070378, compound

Product 1

HCID 53870913HCID 53870913, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Six milliliters (78 millimoles) of thionyl bromide are added to 20 ml of a solution of 5.36 g (32 millimoles) of tricyclo [4.3.1.12,5 ] undecane-1-ol in dry benzene and the entirety is refluxed for 1.5 hours. The reaction mixture is concentrated under reduced pressure and there is further added 20 ml of dry benzene. Reduced pressure concentration is repeated to distill out the excess thionyl chloride completely. The residue is distilled under reduced pressure to collect a fraction boiling at 96°-8° C./2mmHg. Thus 4.53 g (yield 61.3%) of 1-bromotricyclo [4.3.1.12,5 ] undecane are obtained. After cooling, colorless crystals having a melting point of 57.7°-58.5° C. are obtained. The properties of this product are the same as those shown in Example 1.

Workup

  1. temperaturethe entirety is refluxed for 1.5 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure and there
  3. concentrationReduced pressure concentration
  4. distillationto distill out the excess thionyl chloride completely
  5. distillationThe residue is distilled under reduced pressure
  6. customto collect a fraction boiling at 96°-8° C./2mmHg

Sources & evidence

ORD record
ord-71d84457c6d84d6b8966d5c3a010049b
Source dataset
uspto-grants-1978_10
Patent number
US04120906

Reaction notes

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