Boron tribromide → HCID 69441955, compound

HRID 446165Notes

Reaction equation

HRID 446165 reaction equation
B(Br)(Br)Br.[N:5]1([N:10]([CH2:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)[C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)[CH:9]=[CH:8][N:7]=[CH:6]1.C([O-])(O)=O.[Na+]>ClCCl>[OH:17][C:14]1[CH:13]=[CH:12][C:11]([N:10]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=2)[N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 17966433HCID 17966433, compound

Product 1

HCID 69441955HCID 69441955, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of boron tribromide (60 ml, 60.00 mmol) in 20 ml of dichloromethane is added to a cold (0-5° C.) solution of 4-[N-(1H-imidazol-1-yl)-N-(4 methoxyphenyl)amino]methylbenzonitrile (4.60 g, 15.11 mmol). After 1 h at room temperature the mixture was hydrolysed with saturated aqueous NaHCO3, filtered, washed with water (50 ml) and with dichloromethane (20 ml) to give a brown solid (4.00 g). Crystallization from acetone yielded a brown solid (3.00 g, 68%) mp: 150° C.

Workup

  1. filtrationfiltered
  2. washwashed with water (50 ml) and with dichloromethane (20 ml)

Sources & evidence

ORD record
ord-a12d34ee973c445582ac49e41620e36d
Source dataset
uspto-grants-2013_07
Patent number
US08476455B2

Reaction notes

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