Lithium Chloride → 2',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)biphenyl-3-carbaldehyde

HRID 1848798Notes

Reaction equation

Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:4][C:3]=1[CH3:17].[CH:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)=[O:19].[Cl-].[Li+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCCC1>[CH3:17][C:3]1[CH:4]=[C:5]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:7]([CH3:8])[C:2]=1[C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:18]=[O:19])[CH:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzene (0.10 g), 3-formylphenylboronic acid (0.05 g, 1.05 eq), lithium chloride (0.026 g, 2.0 eq), palladium acetate (1.4 mg, 2 mol %) and tri-tert-butylphosphonium tetrafluoroborate (1.8 mg, 2 mol %) were charged in a glass tube, and tetrahydrofuran (1 mL) and water (0.5 mL) were added thereto. After argon substitution, the mixture was stirred at 60° C. for 3 hr. The obtained reaction mixture was analyzed by high performance liquid chromatography to find the title compound (82.9% peak area).

Workup

customThe obtained reaction mixture

Sources & evidence

ORD record: ord-b72c6ff59c1547339266ca8c3c9208d4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952185B2

Reaction notes

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