4-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride) → HCID 85897477, compound

HRID 1180351Notes

Reaction equation

HRID 1180351 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([CH:14]=[O:15])=[C:9]([Cl:16])[CH:8]=1)(=O)=O.[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C>>[Cl:16][C:9]1[CH:8]=[C:7]([C:30]2[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=2)[CH:12]=[C:11]([Cl:13])[C:10]=1[CH:14]=[O:15]

Participants

3

Reactant 2

HCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 223219473,5-Dichloro-4-formylphenyl trifluoromethanesulfonate

Product 1

HCID 85897477HCID 85897477, compound

Procedure

The title compound was prepared by reacting 3,5-dichloro-4-formyl-phenyl trifluoromethanesulfonate (0.73 g, 2.26 mmol) with 4-tert-butyldimethylsilyloxyphenyl boronic acid (0.80 g, 3.2 mmol) according to method C to yield 0.30 g (50%) of a yellow solid: mp:178-180° C.; 1H NMR (DMSO-d6): δ 6.88 (2H, d, J=8.84 Hz), 7.72 (2H, d, J=8.71 Hz), 7.84 (2H, s), 9.95 (1H, s), 10.38 (1H, s); MS (EI) m/z 266.0/268.0/270.0 (M+).

Sources & evidence

ORD record
ord-1ea31fbb9cda487fb99d1c6330183dad
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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