Hydrogen Bromide → (2R,6R)-(-)-1-bromo-2,6,10-trimethylundecane

HRID 1701240Notes

Reaction equation

HRID 1701240 reaction equation
C(O[CH2:6][C@H:7]([CH3:19])[CH2:8][CH2:9][CH2:10][C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])(C)(C)C.[BrH:20]>>[Br:20][CH2:6][C@H:7]([CH3:19])[CH2:8][CH2:9][CH2:10][C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 12923314(2R,6R)-(+)-1-tert. Butoxy-2,6,10-trimethylundecane

Product 1

HCID 14478568(2R,6R)-(-)-1-bromo-2,6,10-trimethylundecane

Procedure

A mixture of 1 g. (3.7 mmoles) of (2R,6R)-(+)-1-tert. butoxy-2,6,10-trimethylundecane and 10 ml. of 48% aqueous HBr was stirred and heated at reflux for 5.75 hours. The resulting mixture was cooled and worked up by ether extraction in the manner of Example 1 giving 0.9 g. of crude product. This material was chromatographed on 30 g. of silica gel. Elution with 49:1 parts by volume hexane-ether gave the (2R,6R)-(-)-1-bromo-2,6,10-trimethylundecane which was evaporatively distilled yielding 0.748 g. (73.4%) of a colorless oil, b.p. 83°-85° C. (bath temperature) (0.15 mm Hg).

Workup

  1. additionA mixture of 1 g
  2. temperatureheated
  3. temperatureat reflux for 5.75 hours
  4. temperatureThe resulting mixture was cooled
  5. extractionworked up by ether extraction in the manner of Example 1 giving 0.9 g
  6. customThis material was chromatographed on 30 g
  7. washElution with 49:1 parts by volume hexane-ether

Sources & evidence

ORD record
ord-82664379b32f479d9d4be832b6b558bd
Source dataset
uspto-grants-1980_03
Patent number
US04191842

Reaction notes

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