Triethylsilane → 5-Bromo-3-ethyl-2-hydroxybenzoic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12](O)[CH3:13])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][CH3:13])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
974 mg (3.73 mmol) of 5-bromo-2-hydroxy-3-(1-hydroxy-ethyl)-benzoic acid was dissolved in trifluoroacetic acid under nitrogen. 715 μL (521 mg, 4.48 mmol) of triethyl silane was added and the resulting mixture was heated to 90° C. for 2 h. The mixture was evaporated and the residue purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 563 mg (2.30 mmol, 62%) of 5-bromo-3-ethyl-2-hydroxy-benzoic acid as a colorless solid. 1H-NMR (500 MHz, d6-DMSO): δ 7.73 (d, 1H), 7.57 (d, 1H), 2.61 (q, 2H), 1.15 (t, 3H); MS: m/z 243.0+244.9 (M+H+).
Workup
- customThe mixture was evaporated
- customthe residue purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-12635ae8c4df46ea9e5b55cc9c65d9fc
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709645B2
Reaction notes
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