Hydrochloric Acid → 2-Methoxy-5-chloro-alpha-isopropylbenzyl cyanide

HRID 1155973Notes

Reaction equation

HRID 1155973 reaction equation
[H-].[Na+].Br[CH:4]([CH3:6])[CH3:5].[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=1[CH2:11][C:12]#[N:13].Cl>CN(C)C=O.O>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=1[CH:11]([C:12]#[N:13])[CH:4]([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 7131175(5-Chloro-2-methoxyphenyl)acetonitrile

Product 1

HCID 205362052-Methoxy-5-chloro-alpha-isopropylbenzyl cyanide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (2.4 g) in dimethylformamide (100 ml) was added a solution of 2-bromopropane and 2-methoxy-5-chlorobenzyl cyanide (18.2 g) in dry dimethylformamide (50 ml), keeping the temperature at 20°-30° C. The mixture was then stirred for 30 minutes, water was added cautiously, and the mixture was then poured into ice-water. Hydrochloric acid was then added and the mixture was extracted with dichloromethane, washed with water then with sodium chloride solution, then dried over magnesium sulphate, filtered, and the solvent was then removed to give 25 g of a brown oil. Distillation gave the title product (15 g) as a colourless oil, bp 180° C./20 mm Hg.

Workup

  1. customat 20°-30° C
  2. extractionthe mixture was extracted with dichloromethane
  3. washwashed with water
  4. dry with materialwith sodium chloride solution, then dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent was then removed

Sources & evidence

ORD record
ord-0d16915b9d7e4f1d8bfe67e0a2aaee2a
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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