Hydrochloric Acid → 1-Cyano-1-(2-methoxy-3,5-dibromophenyl)cyclohexane

HRID 1155977Notes

Reaction equation

HRID 1155977 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]Br.[Br:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([CH2:18][C:19]#[N:20])[C:12]=1[O:21][CH3:22].Cl>CN(C)C=O.O>[C:19]([C:18]1([C:13]2[CH:14]=[C:15]([Br:17])[CH:16]=[C:11]([Br:10])[C:12]=2[O:21][CH3:22])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 205361852,4-Dibromo-6-cyanomethylanisole

Product 1

HCID 205362401-Cyano-1-(2-methoxy-3,5-dibromophenyl)cyclohexane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (7 g) in dry dimethylformamide (200 ml) was added a solution of 1,5-dibromopentane (20 ml) and the product of stage (d) in dimethylformamide (40 ml), keeping the temperature at 20°-30° C. The mixture was stirred for 30 minutes, water was added cautiously, and was then poured into ice water. Hydrochloric acid was added and the mixture was extracted with dichloromethane, washed with water and brine, dried over magnesium sulphate and filtered, and the solvent was removed to give a pale brown oil which slowly crystallised. Recrystallisation from ethanol gave the title product as yellow crystalls, mp 100°-102° C.

Workup

  1. customat 20°-30° C
  2. extractionthe mixture was extracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent was removed
  7. customto give a pale brown oil which
  8. customslowly crystallised
  9. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-f62a0966a0b043cb8fd7d532d1c5cc4c
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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