1,2-Dibromoethane → HCID 53754834, compound

HRID 975267Notes

Reaction equation

HRID 975267 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:17][OH:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16].[OH-].[Na+].[Br:21][CH2:22][CH2:23]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:21][CH2:22][CH2:23][O:18][N:17]=[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 131719894HCID 131719894, compound

Product 1

HCID 53754834HCID 53754834, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

To a mixture of the above oxime (7.0 g, 29 mmol), 1,2-dibromoethane (50 ml) and N,N,N,N-tetrabutylammonium bromide (1.0 g, 3 mmol) was carefully added 9N sodium hydroxide (33 ml) while the temperature was kept below 20° C. After stirring at ambient temperature for 3 h the phases were separated and the organic phase was washed with water (2×100 ml) and saturated aqueous ammonium chloride (30 ml). The solvent was evaporated in vacuo and the residue co-evaporated in vacuo with absolute ethanol (100 ml) to give 8.1 g of 1,2-bis(2-fluorophenyl)ethanone O-(2-bromoethyl)oxime.

Workup

  1. customwas kept below 20° C
  2. customwere separated
  3. washthe organic phase was washed with water (2×100 ml) and saturated aqueous ammonium chloride (30 ml)
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-efd0914945744d5f9229b9dc0335b031
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Reaction notes

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