4-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride) → HCID 85977671, compound

HRID 1180336Notes

Reaction equation

HRID 1180336 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](OS(C(F)(F)F)(=O)=O)=[C:5]([CH3:17])[CH:4]=1)=[O:2].[Si]([O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(C(C)(C)C)(C)C>>[OH:25][C:26]1[CH:31]=[CH:30][C:29]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][C:5]=2[CH3:17])=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 187791834-Formyl-2-methylphenyl trifluoromethanesulfonate

Product 1

HCID 85977671HCID 85977671, compound

Procedure

The title compound was prepared by reacting trifluoro-methanesulfonic acid 4-formyl-2-methyl-phenyl ester (9.3 mmol) with 4-tert-butyl-dimethylsilyoxyphenylboronic acid (2.35 g, 9.3 mmol) according to Method B to yield 1.12 mg (57%, over two steps) of yellowish solid: mp 94-96° C.; 1H NMR (DMSO-d6): ): δ 2.33 (3H, s), 6.86 (2H, d, J=8.55 Hz), 7.22 (2H, d, J=8.51 Hz), 7.39 (1H, d, J=7.81 Hz), 7.61 (1H, d, J=7.82 Hz), 7.81 (1H, s), 9.65 (1H, s), 10.00 (1H, s); IR 1670 cm−1; MS (ESI) m/z 211 (M−H)−, 213 (M+H)+.

Workup

  1. customto yield 1.12 mg (57%, over two steps) of yellowish solid

Sources & evidence

ORD record
ord-be8dbdf03ef4486cb3849b571a4fd1fd
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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