Dibromomethane → HCID 19869708, compound

HRID 330304Notes

Reaction equation

HRID 330304 reaction equation
[CH2:1]([C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])([CH2:8]CCC)[C:6]#[N:7])[CH2:2][CH2:3][CH3:4].C(Br)[Br:21].[OH-].[Na+]>CS(C)=O>[Br:21][CH2:8][C:5]([C:6]#[N:7])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 3024DibromomethaneHCID 14798Sodium HydroxideHCID 53697103HCID 53697103, compound

Product 1

HCID 19869708HCID 19869708, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 5 liter three neck round bottom flask equipped with mechanical stirrer was charged with 500 grams (2.46 moles, 1.0 ec.) of alpha-n-butyl-alpha-(2-methoxyphenyl) hexanenitrile and 2500 ml of DMSO and 513 grams of CH2Br2 (2.95 moles, 1.20 ec.). To the reaction was added dropwise over 3 hours 394 grams (4.92 moles, 2.0 eq.) of 50% NaOH. Upon addition of the base the reaction exothermed to 55° C. and was maintained at that temperature during the addition and for two hours following the completion of the addition. The reaction was 90% complete and was quenched by the addition of water. The product was isolated with ether and washed with water and brine. Distillation of the crude material gave 478 grams of product (66% yield, 90% pure) as a colorless liquid.

Workup

  1. additionUpon addition of the base
  2. customthe reaction exothermed to 55° C.
  3. temperaturewas maintained at that temperature during the addition and for two hours
  4. additionthe completion of the addition
  5. customwas quenched by the addition of water
  6. customThe product was isolated with ether
  7. washwashed with water and brine
  8. distillationDistillation of the crude material

Sources & evidence

ORD record
ord-f00ee9fbab8f4d74a468090f2ba8b4c5
Source dataset
uspto-grants-1990_01
Patent number
US04895865

Reaction notes

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