Bromine → 1-Bromo-2-chloro-4-ethoxy-3-fluorobenzene

HRID 2098999Notes

Reaction equation

HRID 2098999 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH3:10])[C:3]=1[F:11].[Br:12]Br>>[Br:12][C:7]1[CH:6]=[CH:5][C:4]([O:8][CH2:9][CH3:10])=[C:3]([F:11])[C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 24408BromineHCID 596780871-Chloro-3-ethoxy-2-fluorobenzene

Product 1

HCID 534149831-Bromo-2-chloro-4-ethoxy-3-fluorobenzeneYield 87.9%

Procedure

504 g of the compound (b44) was added to a reactor in a nitrogen atmosphere, to which 434 g of bromine was added dropwise over 1 hour in a temperature range of 20 to 40° C., followed by stirring for 30 minutes. The resulting reaction mixture was washed with a saturated sodium thiosulfate aqueous solution, a 10% sodium hydroxide aqueous solution, and water. The residue was subjected to fractional distillation under reduced pressure to obtain 605 g of 1-bromo-2-chloro-4-ethoxy-3-fluorobenzene (C12). The resulting compound (C12) was white solid and had a melting point of 48.0 to 48.5° C. and a boiling point of 88 to 90° C./1 mmHg.

Workup

  1. additionwas added dropwise over 1 hour in a temperature range of 20 to 40° C.
  2. customThe resulting reaction mixture
  3. washwas washed with a saturated sodium thiosulfate aqueous solution
  4. distillationThe residue was subjected to fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-48dbce22027e49a79b8a596da6e7d3fb
Source dataset
uspto-grants-2009_08
Patent number
US07569258B2

Reaction notes

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