Potassium Carbonate → 5-Bromo-2-[(2-fluorophenyl)methoxy]benzonitrile

HRID 2264819Notes

Reaction equation

HRID 2264819 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Br.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[F:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 27570145-Bromo-2-hydroxybenzonitrile

Product 1

HCID 226837045-Bromo-2-[(2-fluorophenyl)methoxy]benzonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-bromo-2-hydroxybenzonitrile (3.31 g, 16.71 mmol), synthesized as described in J. Org. Chem. 1997, 13, 4504-4506, 2-fluorobenzylbromide (commercially available, 2.02 ml, 3.16 g, 16.71 mmol) and potassium carbonate (3.46 g, 25.06 mmol) was stirred overnight at room temperature. Then diethylether was added and the solution was washed with water, 1M NaOH and brine. The organic layer was dried (Na2SO4), filtered and evaporated to afford the title compound (4.74 g, 92%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.0 (M, 1H), 7.9 (m, 1H), 7.6 (m, 1H), 7.5-7.3 (m, 2H), 7.2 (m, 2H), 5.3 (s, 2H).

Workup

  1. washthe solution was washed with water, 1M NaOH and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-b8f4965a1ce64d77afc5e627f1378c18
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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