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

HRID 1848799Notes

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].O[Li].O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[Pd](Cl)Cl.O.CN(C)C(=O)C>[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 (1.0 g), 3-formylphenylboronic acid (0.49 g, 1.05 eq), LiOH.H2O (0.26 g, 2.0 eq), palladium chloride (11 mg, 2 mol %) and 2-(dicyclohexylphosphino)biphenyl (44 mg, 4 mol %) were charged in a reaction container, and N,N-dimethylacetamide (10 mL) and water (5 mL) were added thereto. After nitrogen 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 (94.0% peak area).

Workup

additionwere added
customThe obtained reaction mixture

Sources & evidence

ORD record: ord-f547e9976e5841fcb4d9638ac0d3dfa0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952185B2

Reaction notes

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