4-(Bromomethyl)heptane → 1-Nitro-2-propylpentane

HRID 1883974Notes

Reaction equation

HRID 1883974 reaction equation
[N:1]([O-:3])=[O:2].[Na+].Br[CH2:6][CH:7]([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10]>CS(C)=O>[N+:1]([CH2:6][CH:7]([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 5459644-(Bromomethyl)heptaneHCID 23668193Sodium Nitrite

Product 1

HCID 235087641-Nitro-2-propylpentaneYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of sodium nitrite (30.6 g, 0.43 mol) in DMSO (700 ml) was added 1-bromo-2-propylpentane (49 g, 0.254 mol). The mixture was stirred overnight at room temperature and poured into ice water (700 g). The mixture was extracted with ether (4×250 ml), the organic layers were combined, washed with water (2×500 ml), brine (500 ml), dried and concentrated in vacuo to furnish 37.4 g (93%) of 1-nitro-2-propylpentane which was 85% pure based on 1H NMR data.

Workup

  1. extractionThe mixture was extracted with ether (4×250 ml)
  2. washwashed with water (2×500 ml), brine (500 ml)
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04a2b08cc42c4ba5a5b29c7f12aaf69e
Source dataset
uspto-grants-2004_07
Patent number
US06762316B1

Reaction notes

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