2-Bromophenol → HCID 11011179, compound

HRID 730076Notes

Reaction equation

HRID 730076 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].F[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 11011179HCID 11011179, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromophenol (6.0 mL, 51.7 mmol) in DMF (80 mL) was added potassium carbonate (7.16 g, 51.7 mmol), and the mixture was allowed to stir for 10 min ar rt. 2-Fluorobenzonitrile (5.62 mL, 82.6 mmol) was added and the mixture was heated to 100° C. for 40 h. The mixture was allowed to cool to rt, poured onto ice, filtered, washed with water, and dried to yield 13.0 g (91.7%) of title compound 2-(2-bromophenoxy)-benzonitrile 1j.

Workup

  1. temperaturethe mixture was heated to 100° C. for 40 h
  2. temperatureto cool to rt
  3. additionpoured onto ice
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f3304e13f48a45cca844e33d8e499f57
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

Loading…