Dichloromethane → HCID 67515500, compound

HRID 2173232Notes

Reaction equation

HRID 2173232 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:12]Br.C(Cl)Cl>C(Cl)(Cl)Cl>[Br:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]([F:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 6398782-Fluoro-4-methoxybenzonitrile

Product 1

HCID 67515500HCID 67515500, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 2-fluoro-4-methoxybenzonitrile (2.97 g, 19.0 mmol) in CHCl3 (30 mL) was added Br2 (2 mL), and the mixture was stirred at ambient temperature for 4 days. The mixture was diluted by DCM and washed with saturated NaHCO3, water, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified with fast column chromatograph to give 5-bromo-2-fluoro-4-methoxybenzonitrile. 1H-NMR (300 MHz, CDCl3) δ ppm 7.76 (d, J=7.2 Hz, 1H), 6.73 (d, J=10.5 Hz, 1H), 3.96 (s, 3H).

Workup

  1. washwashed with saturated NaHCO3, water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with fast column chromatograph

Sources & evidence

ORD record
ord-3c498bad047841c9b2d66f90433549ea
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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