2-(Bromomethyl)-1,3-difluorobenzene → HCID 117858409, compound

HRID 1486233Notes

Reaction equation

HRID 1486233 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4]Br.[OH:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 178428601HCID 178428601, compound

Product 1

HCID 117858409HCID 117858409, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.00 g (24.2 mmol, 1.0 eq.) of 2,6-difluorobenzyl bromide [CAS No: 85118-00-9] and 3.16 g (29.0 mmol, 1.2 eq.) of 2-hydroxy-4-methylpyridine [CAS No: 13466-41-6] was dissolved in 50 ml of THF. The solution was admixed with 7.99 g (29.0 mmol, 1.2 eq.) of silver carbonate and the mixture was heated to reflux with exclusion of light overnight. Subsequently, the reaction mixture was filtered through kieselguhr and eluted with ethyl acetate, and the filtrate was concentrated. The crude product was purified by means of Biotage Isolera (100 g silica gel cartridge, cyclohexane/ethyl acetate gradient, 0% to 10% ethyl acetate). 3.51 g of the title compound were obtained (61% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux with exclusion of light overnight
  3. filtrationSubsequently, the reaction mixture was filtered through kieselguhr
  4. washeluted with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by means of Biotage Isolera (100 g silica gel cartridge, cyclohexane/ethyl acetate gradient, 0% to 10% ethyl acetate)

Sources & evidence

ORD record
ord-b4e113f6221b4228a96b9e6c04482d24
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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