4-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride) → HCID 86618215, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[Si:18]([O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>>[Si:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C:4]2[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[C:2]([Cl:1])[CH:3]=2)=[CH:30][CH:31]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]Participants
3
Procedure
The title compound was prepared by reacting trifluoro-methanesulfonic acid 3-chloro-4-formyl-phenyl ester (1.78 g, 6.18 mmol) with 4-tert-butyl-dimethylsilyoxyphenylboronic acid (2.03 g, 8.03 mmol) according to Method B to yield 0.92 g (43%) of white solid: mp 38-39° C.; 1H NMR (DMDO-d6); δ 0.23 (6H, s), 0.97 (9H, s), 6.98 (2H, d, J=8.79 Hz), 7.74 (2H, d, J=8.79 Hz), 7.81 (1H, d, J=7.81 Hz), 7.89 (1H, d, J=1.95 Hz), 7.91 (1H, d, J=7.81 Hz), 10.34 (1H, s); MS (ESI) m/z 231/233 (M−H)−(deprotected product ion).
Sources & evidence
- ORD record
- ord-7bb61c06dc4b4c32a10c396ae49373a4
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279600B2
Reaction notes
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