Dimethylformamide → 4-(4-Bromobutyl)-2,2-dimethyl-1,3-dioxolane

HRID 1577701Notes

Reaction equation

HRID 1577701 reaction equation
[CH3:1][C:2]1([CH3:22])[O:6][CH:5]([CH2:7][CH2:8][CH2:9][CH2:10]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:4][O:3]1.CN(C)C=O.[Br-:28].[Li+]>O>[Br:28][CH2:10][CH2:9][CH2:8][CH2:7][CH:5]1[CH2:4][O:3][C:2]([CH3:22])([CH3:1])[O:6]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 82050Lithium BromideHCID 127708652,2-Dimethyl-4-(4-p-toluenesulfonyloxybutyl)-1,3-dioxolane

Product 1

HCID 46572524-(4-Bromobutyl)-2,2-dimethyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 220 g. of 2,2-dimethyl-4-(4-p-toluenesulfonyloxybutyl)-1,3-dioxolane in 800 ml. of dimethylformamide at 0° C. is added 115 g. of anhydrous lithium bromide in portions during 5 minutes. The resulting mixture is stirred at ambient temperature for 22 hours, diluted with water, and extracted with ether. The extract is washed with sodium bicarbonate solution, water, and brine; dried over magnesium sulfate; and concentrated. The residue is distilled to give a colorless liquid, b.p. 71°-74° C. (0.2 mm.).

Workup

  1. extractionextracted with ether
  2. washThe extract is washed with sodium bicarbonate solution, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationand concentrated
  5. distillationThe residue is distilled
  6. customto give a colorless liquid, b.p. 71°-74° C. (0.2 mm.)

Sources & evidence

ORD record
ord-d0553c1d58cc4d04a28307f163f09552
Source dataset
uspto-grants-1981_09
Patent number
US04288632

Reaction notes

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