Dimethylformamide → HCID 15569719, compound

HRID 2308401Notes

Reaction equation

HRID 2308401 reaction equation
[Br-:1].[Na+].CN(C=O)C.S([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)([O-])(=O)=O>O>[Br:1][CH2:13][CH2:14][CH:15]([CH3:16])[CH2:17][CH2:18][CH2:12][CH2:17][CH2:18][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 85570p-ToluenesulfonateHCID 253881Sodium Bromide

Product 1

HCID 15569719HCID 15569719, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridine (20 ml) was added to a methylene chloride (50 ml) solution of the 3-methyldodecan-1-ol (4″) (12.8 g, 63.9 mols), and p-toluenesulfonyl chloride (12.8 g, 67.1 mmols) was further added under ice-cooling. The reaction mixture was stirred overnight at 4° C., then poured into diluted hydrochloric acid, and extracted with hexane. The organic layer was washed (water, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride), dried (magnesium sulfate), and concentrated under reduced pressure to obtain 21.7 g of a tosylate. Sodium bromide (9.9 g, 96 mols) was added to a DMF solution (100 ml) of the resulting tosylate, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and extracted with hexane. The organic layer was washed (water and a saturated aqueous solution of sodium chloride), dried (magnesium sulfate), and concentrated under reduced pressure to obtain 1-bromo-3-methyldodecane (5″) (15.1 g, 90%). 1H-NMR (90 MHz, CDCl3) 0.8-1.0 (6H,m,Me), 1.0-2.0 (19H,m,2˜11-H), 3.43 (2H,br t,J=7,1-H).

Workup

  1. extractionextracted with hexane
  2. washThe organic layer was washed (water
  3. dry with materiala saturated aqueous solution of sodium chloride), dried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e888ff2189bf4775ba71f98c0a370f70
Source dataset
uspto-grants-2004_12
Patent number
US06835846B2

Reaction notes

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