Sodium hydride → 1-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester

HRID 1258833

Reaction equation

HRID 1258833 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([OH:9])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].C1OCCOCCOCCOCCOC1.[Br:27][C:28]1[CH:33]=[CH:32][C:31](O)=[C:30]([N+:35]([O-:37])=[O:36])[C:29]=1F>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([O:9][C:31]2[CH:32]=[CH:33][C:28]([Br:27])=[CH:29][C:30]=2[N+:35]([O-:37])=[O:36])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylateHCID 534048764-Bromo-3-fluoro-2-nitrophenol

Product 1

HCID 583407841-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl esterYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl-1-hydroxycyclopropane carboxylate (2.93 g, 20.5 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 981 mg, 24.5 mmol) under argon atmosphere. After 10 min, 15-crown-5 (0.2 mL) followed by 4-bromo-2-nitro-fluorophenol (4.5 g, 20.5 mmol) were added. The reaction mixture was stirred at room temperature overnight then quenched by the addition of methanol (1.5 mL) and diluted with ethyl acetate. The mixture was washed with brine, and the organic layer was dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography to give 1-(4-bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester (3.51 g).

Workup

  1. additionwere added
  2. customthen quenched by the addition of methanol (1.5 mL)
  3. additiondiluted with ethyl acetate
  4. washThe mixture was washed with brine
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-3e96af10336743b39d11cdf382a2ee31
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Linked notes

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