4-Formylphenylboronic Acid → HCID 57937848, compound

HRID 1435065Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[CH:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13]>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=2[CH3:11])=[CH:16][CH:15]=1)=[O:13]

Participants

Conditions

Temperature: 95 °C

Procedure

4-Bromo-3-methyl-benzamide (15.02 g), 70 mmol), 4-formylphenylboronic acid (14.039, 91 mmol) and palladium tetrakis(triphenylphosphine) (5.03 g, 4 mmol) were combined in 1,2-dimethoxy ethane (5 ml) and 2M aqueous sodium carbonate (2.5 ml). After heating at 95° C. for 48 hours, the reaction mixture was cooled to ambient temperature and passed through a plug of Celite, rinsing with 1,2-dimethoxy ethane. The volatiles were removed under reduced pressure to yield 16 g of the title compound (I-4a) as a colorless solid.

Workup

temperaturethe reaction mixture was cooled to ambient temperature
washrinsing with 1,2-dimethoxy ethane
customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-b46535751b334f83a6a75da3e59ad255
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615651B2

Reaction notes

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