Nitromethane → HCID 118342971, compound

HRID 2202716Notes

Reaction equation

HRID 2202716 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([Cl:17])[C:9]=1[CH:10]=[O:11].[N+:18]([CH3:21])([O-:20])=[O:19]>C1COCC1>[Cl:7][C:8]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([Cl:17])[C:9]=1[CH:10]([OH:11])[CH2:21][N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 11430Potassium CarbonateHCID 189456742,6-Dichloro-3-fluorobenzaldehyde

Product 1

HCID 118342971HCID 118342971, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 3-necked 100 mL RBF, freshly ground potassium carbonate (0.486 g, 3.51 mmol) was added to a solution of 2,6-dichloro-3-fluorobenzaldehyde (2.26 g, 11.71 mmol) in THF (12 ml) at room temperature. Then nitromethane (8.88 ml, 164 mmol) was added. The mixture was stirred at room temperature for 2 h. The mixture was quenched with water (15 mL) and extracted with EtOAc (3×15 mL). The combined organic layer washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 1-(2,6-dichloro-3-fluorophenyl)-2-nitroethanol (2.97 g, 11.69 mmol, 100% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.36 (dd, J=8.9, 4.8 Hz, 1H), 7.17 (dd, J=8.9, 7.8 Hz, 1H), 6.27 (m, 1H), 5.19 (dd, J=13.3, 10.1 Hz, 1H), 4.57 (dd, J=13.3, 3.4 Hz, 1H), 3.20 (br. s., 1H).

Workup

  1. customThe mixture was quenched with water (15 mL)
  2. extractionextracted with EtOAc (3×15 mL)
  3. washThe combined organic layer washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76d1230a3b174a0b91b6dd693eb4c267
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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