Sodium Thiosulfate → 6-Bromo-2,2',4'-trifluoro-3-hydroxybiphenyl-4-carbaldehyde
Reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[F:12][C:13]1[C:18]([OH:19])=[C:17]([CH:20]=[O:21])[CH:16]=[CH:15][C:14]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[F:29].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Br:1][C:15]1[C:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])=[C:13]([F:12])[C:18]([OH:19])=[C:17]([CH:20]=[O:21])[CH:16]=1Participants
Procedure
Dibromoisocyanuric acid (2.25 g) was added at room temperature to a DMF (90 mL) solution of 2,2′,4′-trifluoro-3-hydroxybiphenyl-4-carbaldehyde (3.29 g), and the mixture was stirred at the same temperature as above for 3 hours in a nitrogen atmosphere. A saturated aqueous solution of sodium thiosulfate was added to the reaction mixture at room temperature, followed by extraction with ethyl acetate. The organic layer was separated, then washed with water and saturated saline in this order, and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) and silica gel column chromatography (diol, hexane/ethyl acetate) to obtain the title compound (3.15 g).
Workup
- extractionfollowed by extraction with ethyl acetate
- customThe organic layer was separated
- washwashed with water and saturated saline in this order
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) and silica gel column chromatography (diol, hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-bb015b9cc6e141439fa052410e8ef4d1
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120777B2
Reaction notes
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