Sodium Carbonate → 2',4'-Difluoro-3-hydroxy[1,1'-biphenyl]-4-carbaldehyde

HRID 531140

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[CH:3]=1.[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-2-hydroxybenzaldehyde (7.5 g), (2,4-difluorophenyl)boronic acid (8.84 g), tris(dibenzylideneacetone)dipalladium (0) (1.367 g), 2M aqueous sodium carbonate solution (56.0 mL) and dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.53 g) in toluene (70 mL) was stirred at 100° C. under nitrogen atmosphere overnight. The mixture was diluted with ethyl acetate and water. The organic layer was separated and concentrated in vacuo. The residue was passed through a silica gel pad and concentrated in vacuo. The residue was crystallized from methanol-water (80 mL-20 mL) to give the title compound (8.50 g).

Workup

customThe organic layer was separated
concentrationconcentrated in vacuo
concentrationconcentrated in vacuo
customThe residue was crystallized from methanol-water (80 mL-20 mL)

Sources & evidence

ORD record: ord-298f52b8b3634dd3988285784454a942
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Linked notes

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