Water → 5-Benzyloxy-2-chloro-nitrobenzene

HRID 1795870Notes

Reaction equation

HRID 1795870 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[CH2:1]([O:16][C:13]1[CH:14]=[CH:15][C:10]([Cl:9])=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 110436225-Benzyloxy-2-chloro-nitrobenzeneYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This was prepared as follows:- A solution of benzyl bromide (10.26 g; 60 mmol) and 4chloro-3-nitrophenol (8.7 g; 50 mmol) in DMF (250 ml) was treated with Na2CO3 (10.6 g; 0.1 mol) and the mixture was stirred at room temperature for 3 days. The mixture was poured into water and extracted with Et2O. The organic phase was washed with brine and dried over MgSO4. The residue was purified by flash chromatography eluting with CH2Cl2 to give 5-benzyloxy-2-chloro-nitrobenzene as a pale yellow solid (12.32 g).

Workup

  1. customThis was prepared
  2. extractionextracted with Et2O
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customThe residue was purified by flash chromatography
  6. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-c72694a60dbf44c58f87db05f0258986
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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