Benzyl Chloride → HCID 13596237, compound

HRID 325747Notes

Reaction equation

HRID 325747 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([OH:11])=[C:4]([O:12][CH3:13])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>S1(CCCC1)(=O)=O.O>[CH2:20]([O:11][C:5]1[C:4]([O:12][CH3:13])=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[N+:8]([O-:10])=[O:9])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 22448999HCID 22448999, compound

Product 1

HCID 13596237HCID 13596237, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31347SulfolaneSolvent

Procedure

A mixture of 4-bromo-2-methoxy-6-nitrophenol (7.0 g), anhydrous potassium carbonate (2.12 g) and benzyl chloride (3.93 g) in dry sulpholane (70 ml) was stirred at 90°-95° C. for 24 hours. The mixture was then diluted with water (300 ml) and the resulting oil was extracted with diethyl ether (3×50 ml). The combined ethereal extracts were washed with aqueous sodium carbonate solution (2 N; 2×50 ml) and then with water (3×20 ml), dried over anhydrous sodium sulphate and evaporated in vacuo to give a solid, which was recrystallised from ethanol to give 2-benzyloxy-5-bromo-3-methoxynitrobenzene (7.7 g), m.p. 74°-76° C.

Workup

  1. extractionthe resulting oil was extracted with diethyl ether (3×50 ml)
  2. washThe combined ethereal extracts were washed with aqueous sodium carbonate solution (2 N; 2×50 ml)
  3. dry with materialwith water (3×20 ml), dried over anhydrous sodium sulphate
  4. customevaporated in vacuo
  5. customto give a solid, which
  6. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-b2587e418d604f8cb41f7922dd5b2b88
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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