Sodium hydride → 5-Bromo-1,2-difluoro-3-[(4-methoxyphenyl)methoxy]benzene

HRID 2403374Notes

Reaction equation

HRID 2403374 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.[H-].[Na+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[C:5]([F:9])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 27733075-Bromo-2,3-Difluorophenol

Product 1

HCID 666176725-Bromo-1,2-difluoro-3-[(4-methoxyphenyl)methoxy]benzeneYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-bromo-2,3-difluorophenol (1.0 g) in tetrahydrofuran (10 ml) under nitrogen was added sodium hydride, 60% dispersion in mineral oil (0.20 g). The solution was stirred at room temperature. After 30 minutes a solution of 4-methoxybenzylbromide (0.96 g) was added in tetrahydrofuran (7 ml). The reaction mixture was stirred at 50° C. overnight. The reaction mixture was partitioned between dichloromethane and brine, then dried (MgSO4), the solvents were removed in vacuo to give a crude residue. This crude residue was purified using flash chromatography to give 5-bromo-1,2-difluoro-3-(4-methoxy-benzyloxy)-benzene (0.76 g).

Workup

  1. stirringThe reaction mixture was stirred at 50° C. overnight
  2. customThe reaction mixture was partitioned between dichloromethane and brine
  3. dry with materialdried (MgSO4)
  4. customthe solvents were removed in vacuo
  5. customto give a crude residue
  6. customThis crude residue was purified

Sources & evidence

ORD record
ord-d11ed2b13996436ba81890f7d1d57768
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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