Sodium hydride → HCID 64037206, compound

HRID 2403378Notes

Reaction equation

HRID 2403378 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.[H-].[Na+].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([O:8][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 8203925-Bromo-2-chlorophenol

Product 1

HCID 64037206HCID 64037206, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-bromo-2-chlorophenol (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 (0.97 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 4-bromo-1-chloro-2-(4-methoxy-benzyloxy)-benzene (0.96 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-7d846e70869e422ea5b091fc6dcc353c
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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