Hydrogen Bromide → (2-Bromoethyl)cyclohexane

HRID 1965814Notes

Reaction equation

HRID 1965814 reaction equation
S(=O)(=O)(O)O.[BrH:6].[CH:7]1([CH2:13][CH2:14]O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>>[Br:6][CH2:14][CH2:13][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 205082-Cyclohexylethanol

Product 1

HCID 15440(2-Bromoethyl)cyclohexaneYield 840.2%

Procedure

In a 1 l-roundbottom flask equipped with a reflux condenser 164 g concentrated sulphuric acid and 200 g hydrobromic acid (48% in water) were added subsequently under cooling with an ice bath to 88.7 g (0.693 mole) 2-cyclohexyl-ethanol. The mixture was refluxed for 6 h and after cooling to room temperature it was poured onto 400 g of ice. The aqueous phase was extracted with 400 ml pentane. The organic layer was washed with a 2 M NaOH-solution and with water, dried over magnesium sulphate, and the solvent was removed in vacuo. The product was distilled in vacuo to yield 1112.7 g (85%) of (2-bromo-ethyl)-cyclohexane as a colourless oil 1H-NMR (4-MHz, CDCl3): δ=3.40 (2H, t, CH2Br), 1.73-1.61 (m, 7H), 1.44 (m, 1H), 1.26-1.11 (m, 3H), 0.92-0.84 (m, 2H) ppm.

Workup

  1. additionwere added subsequently
  2. temperatureThe mixture was refluxed for 6 h
  3. extractionThe aqueous phase was extracted with 400 ml pentane
  4. washThe organic layer was washed with a 2 M NaOH-solution and with water
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent was removed in vacuo
  7. distillationThe product was distilled in vacuo

Sources & evidence

ORD record
ord-63ca070c84dc4fc89b9b2619811dd64e
Source dataset
uspto-grants-2013_04
Patent number
US08415492B2

Reaction notes

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