3,7-Dimethyl-1-octanol → 1-Bromo-3,7-dimethyloctane

HRID 1176159Notes

Reaction equation

HRID 1176159 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:3][CH2:4]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:31]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH2:3][CH2:4][Br:31]

Participants

5

Reactant 3

HCID 77923,7-Dimethyl-1-octanolHCID 11776TriphenylphosphineHCID 67184N-bromobutanimide

Product 1

HCID 1379141-Bromo-3,7-dimethyloctane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,7-dimethyl-1-octanol (50.0 ml, 0.264 mol) and triphenylphosphine (86.9 g, 0.331 mol) in 300 ml of CH2Cl2 were added N-bromosuccinimide (56.6 g, 0.318 mol) in portions at 0° C. After stirring at 0° C. for 2 h, the solvent was evaporated. The residue was treated with hexane and filtered. The solids were washed thoroughly with hexane and the combined hexane extracts evaporated. The residue was chromatographed on silica gel with hexane. Yield=54.13 g (93% based on 50.0 ml of 3,7-dimethyl-1-octanol). 1H NMR (360 MHz, CDCl3): δ 3.37-3.50 (m, 2H, —CH2Br), 1.07-1.94 (m, 10H, (CH3)2CHCH2CH2CH2CH(CH3)CH2CH2Br), 0.89 (d, 3H, J=6.5 Hz, —CH3), 0.87 (d, 6H, J=6.8 Hz, —CH3). CI MS m/z: 220.048 (M+) (calcd 220.083).

Workup

  1. customthe solvent was evaporated
  2. additionThe residue was treated with hexane
  3. filtrationfiltered
  4. washThe solids were washed thoroughly with hexane
  5. customthe combined hexane extracts evaporated
  6. customThe residue was chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-cecf8873b21243efae36c050d887ab0a
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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