Dibromomethane → HCID 19756491, compound

HRID 1587769Notes

Reaction equation

HRID 1587769 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH2:18][CH3:19])[C:16]#[N:17])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(Cl)Cl.[CH2:25](Br)[Br:26]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:16]([C:15]([C:12]1[CH:11]=[CH:10][C:9]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:13]=1)([CH2:18][CH3:19])[CH2:25][Br:26])#[N:17]

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 19756489HCID 19756489, compound

Product 1

HCID 19756491HCID 19756491, compound

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

To a solution of 5 g (0.021 mol) 2-[4-(phenylethinyl)phenyl]-butyronitrile in 65 ml CH2Br2 are added, with stirring, 64 g 50% (0.8 mol) NaOH and 5.5 g (0.025 mol) benzyltriethylammoniumchloride. The mixture is stirred for 5 hours at 95°, cooled and 250 ml CH2Cl2 are added. The organic phase is separated off, washed, dried and evaporated in vacuum. The thus obtained title compound is kept for one hour at 70°-80° under high vacuum and crystallises from toluene: ligroine 1:2, m.p. 107°.

Workup

  1. stirringThe mixture is stirred for 5 hours at 95°
  2. temperaturecooled
  3. customThe organic phase is separated off
  4. washwashed
  5. customdried
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-46c63b5b3c5642ffbccc1a59f92e9110
Source dataset
uspto-grants-1993_06
Patent number
US05219876

Reaction notes

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