Sodium Hydroxide → HCID 11426186, compound

HRID 1440530Notes

Reaction equation

HRID 1440530 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].Br.Br[CH2:14][CH2:15][NH2:16].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]1[O:5][CH2:14][CH2:15][N:16]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 874382,6-Difluorobenzoyl chlorideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 11426186HCID 11426186, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2,6-Difluorobenzoyl chloride (100 g, 566 mmol) was added dropwise over 2 h to a vigorously stirred and ice water cooled mixture of 2-bromoethyl amine hydrobromide (116.05 g, 566 mmol), benzyltriethylammonium chloride (5 g, 22.0 mmol), 10% aq NaOH (680 mL, 1.7 mol), and CH2Cl2 (1.5 L). The resulting mixture was stirred at RT overnight, than was washed with water (3×200 mL), dried(MgSO4), concentrated, and kugelrohr distilled to afford 51.8 g of 2-(2,6-difluorophenyl)-2-oxazoline as a colorless oil, a 50% yield.

Workup

  1. stirringThe resulting mixture was stirred at RT overnight
  2. washthan was washed with water (3×200 mL), dried(MgSO4)
  3. concentrationconcentrated
  4. distillationkugelrohr distilled

Sources & evidence

ORD record
ord-bbc0622b6c17492a9b30a8ddaee1733d
Source dataset
uspto-grants-1996_03
Patent number
US05498630

Reaction notes

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