4-Bromobenzaldehyde → HCID 42643333, compound

HRID 1180328Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Si:10]([O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>>[Si:10]([O:17][C:18]1[CH:19]=[CH:20][C:21]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:22][CH:23]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

Reactant 2

HCID 707414-Bromobenzaldehyde

HCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 42643333HCID 42643333, compound

Procedure

The title compound was prepared by reacting 4-bromobenzaldehyde (730 mg, 3.97 mmol) with 4-tert-butyl-dimethylsilyoxyphenylboronic acid (1.3 g, 5.16 mmol) according to Method B to yield 600 mg (48%) of white crystal: 1H NMR (DMSO-d6): δ 0.24 (6H, s), 1.01 (9H, s), 6.94 (2H, d, J=8.54 Hz), 7.53 (2H, d, J=8.56 Hz), 7.72 (2H, d, J=8.19 Hz), 7.93 (2H, d, 8.20 Hz), 10.04 (1H, s).

Sources & evidence

ORD record: ord-60714aa200f04a93a4834bbba94441c7
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279600B2

Reaction notes

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