Bromine → 2-bromo-2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone

HRID 433010Notes

Reaction equation

HRID 433010 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:22]=[CH:21][C:14]3[N:15]=[N:16][N:17]([CH:18]([CH3:20])[CH3:19])[C:13]=3[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[Br:23]Br>C(O)(=O)C>[Br:23][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:9]([C:11]1[CH:22]=[CH:21][C:14]2[N:15]=[N:16][N:17]([CH:18]([CH3:19])[CH3:20])[C:13]=2[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 187608012-(4-Fluoro-phenyl)-1-(3-isopropyl-3h-benzotriazol-5-yl)-ethanone

Product 1

HCID 187607892-bromo-2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 191 mg of 2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone in 2 mL of acetic acid was added 0.64 mL of bromine (1 M in acetic acid). The mixture was heated at 50° C. for 3 hours. The reaction mixture was cooled to 22° C. and concentrated to dryness. The residue was taken-up into ethyl acetate and washed with saturated aqueous sodium bicarbonate, brine; the organic layer was dried (sodium sulfate), filtered and the filtrate was concentrated to give 222 mg of 2-bromo-2-(4-fluoro-phenyl)-1-(3-isopropyl-3H-benzotriazol-5-yl)-ethanone as a light yellow oil. This material was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 22° C.
  2. concentrationconcentrated to dryness
  3. washwashed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialthe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4f30ae2800604409954b23b94c2854d5
Source dataset
uspto-grants-2003_12
Patent number
US06664395B2

Reaction notes

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