Ethanol → Ethyl 5-chloro-2-nitrobenzoate

HRID 1864975Notes

Reaction equation

HRID 1864975 reaction equation
[CH2:1]([OH:3])[CH3:2].C(N(CC)CC)C.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N+:21]([O-:23])=[O:22])=[C:16]([CH:20]=1)[C:17](Cl)=[O:18].O>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:17](=[O:18])[C:16]1[CH:20]=[C:12]([Cl:11])[CH:13]=[CH:14][C:15]=1[N+:21]([O-:23])=[O:22])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8471TriethylamineHCID 27236855-Chloro-2-nitrobenzoyl chloride

Product 1

HCID 603450Ethyl 5-chloro-2-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethanol (1.23 mL), triethylamine (3.05 mL) and tetrahydrofuran (35 mL) was dropwise added a solution of 5-chloro-2-nitrobenzoic acid chloride (4.44 g) obtained in Example 9-4a) in tetrahydrofuran (10 mL) under ice-cooling. The mixture was stirred at room temperature overnight, and water was then added. The solution was diluted with ethyl acetate, and the organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated brine, dried over sodium sulfate and concentrated to give the title compound (4.43 g) as a pale brown solid.

Workup

  1. temperaturecooling
  2. washthe organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16fe8c1f24194a2da8d6763b7f956b94
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

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