Sodium Hydroxide → HCID 24721199, compound

HRID 1770363Notes

Reaction equation

HRID 1770363 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:16](=[O:18])[CH3:17].[Br:19]Br.[OH-].[Na+]>CC(OC)(C)C.C(O)(=O)C>[Br:19][CH2:17][C:16]([C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:7][C:2]=1[Cl:1])=[O:18]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 6774791-[2-Chloro-4-(4-chlorophenoxy)phenyl]ethan-1-one

Product 1

HCID 24721199HCID 24721199, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone (1000 g) was dissolved in MTBE (5000 mL) and a solution of bromine (563 g) in glacial acetic acid (400 mL) was added dropwise at room temperature. After completion of the addition the mixture was stirred for 1 h at room temperature and the pH was adjusted to 7-8 by addition of 10% NaOH solution. The organic layer was separated, extracted twice with MTBE and the combined organic phases were washed with sat. NaHCO3 solution (1×) and brine (2×). The solvent was evaporated and the crude product was used directly in the next step.

Workup

  1. additionAfter completion of the addition the mixture
  2. customThe organic layer was separated
  3. extractionextracted twice with MTBE
  4. washthe combined organic phases were washed with sat. NaHCO3 solution (1×) and brine (2×)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d28a0637a7d54976a9f91daca538b9aa
Source dataset
uspto-grants-2016_02
Patent number
US09247747B2

Reaction notes

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