Sulfuric Acid → 5-Bromo-2,3-dichlorobenzaldehyde
Reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12].S(=O)(=O)(O)O.[Br:23]N1C(=O)CCC1=O>>[Br:23][C:14]1[CH:15]=[C:16]([Cl:17])[C:9]([Cl:8])=[C:10]([CH:13]=1)[CH:11]=[O:12]Participants
5
Procedure
To a TFA solution (0.38 M) of 2,3-dichlorobenzaldehyde (1 eq.) was added sulfuric acid (5 eq.). Over a period of 3 h, N-bromosuccinimide (1.5 eq.) was added portionwise at RT to afford, in the end, a yellow-orange solution. After 72 h, the crude reaction mixture was diluted with 9:1 (v/v) hexanes:ether and then washed sequentially with water, 1 N aq. NaOH, water and brine. The organic extract was dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the title compound as a white solid.
Workup
- customto afford, in the end
- waitAfter 72 h
- customthe crude reaction mixture
- washether and then washed sequentially with water, 1 N aq. NaOH, water and brine
- extractionThe organic extract
- dry with materialwas dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-e7e6070cca8d4dbc82d73ca29c3f6a0a
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889714B2
Reaction notes
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