Hydrogen Bromide → HCID 57572811, compound

HRID 1367602Notes

Reaction equation

HRID 1367602 reaction equation
[CH2:1]([CH:4]([CH2:11][CH2:12][CH3:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]O)[CH2:2][CH3:3].[BrH:14].S(=O)(=O)(O)O>O>[Br:14][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([CH2:11][CH2:12][CH3:13])[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 22492558HCID 22492558, compound

Product 1

HCID 57572811HCID 57572811, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a 50 mL flask containing 6-propylnonan-1-ol (4.92 g, 26.4 mmol) was added hydrobromic acid 48% (12 mL, 105.6 mmol, 4 eq.) and conc. sulfuric acid (1.4 mL, 26.4 mmol, 1 eq.) and the mixture was heated to reflux (95° C.) for 14 h. The reaction was cooled to room temperature before adding H2O (40 mL). The mixture was extracted with dichloromethane (3×120 mL) and the combined organic phases were washed with aqueous sodium bicarbonate (40 mL, 1M). Drying over magnesium sulfate and evaporation gave 1-bromo-6-propylnonane (5.87 g, 89% yield) as a brown liquid. 1H NMR (CDCl3, 400 MHz) d?(ppm): 3.40 (t, J=6.8 Hz, 2H); 1.86 (tt, J=6.8 Hz, J=6.8 Hz, 2H); 1.45-1.35 (m, 2H); 1.34-1.15 (m, 13H); 0.88 (t, J=6.8 Hz, 6H). 13C NMR (CDCl3, 129.9 MHz) d?(ppm): 36.9; 36.0 (2C); 34.0; 33.5; 33.9; 28.7; 25.8; 19.8 (2C); 14.5 (2C).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction was cooled to room temperature
  3. extractionThe mixture was extracted with dichloromethane (3×120 mL)
  4. washthe combined organic phases were washed with aqueous sodium bicarbonate (40 mL, 1M)
  5. dry with materialDrying over magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-1bb6f9d15d5544908871abb6cbfd0d72
Source dataset
uspto-grants-2011_02
Patent number
US07893258B2

Reaction notes

Loading…