Cesium fluoride → 4'-Bromo-4-hydroxy-5-methoxy-biphenyl-2-carbaldehyde

HRID 2252230Notes

Reaction equation

Br[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5].[Br:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[F-].[Cs+]>COCCOC.CO.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:3]([CH:4]=[O:5])=[CH:6][C:7]([OH:12])=[C:8]([O:10][CH3:11])[CH:9]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-bromo-5-hydroxy-4-methoxy-benzaldehyde (1.00 g, 4.32 mmol), 4-bromophenyl boronic acid (1.04 g, 5.18 mmol), Pd(PPh3)4 (0.250 g), and CsF (1.97 g, 12.6 mmol) in DME/MeOH (1:1, 65 mL) was heated at 70° C. overnight. The mixture was diluted with CH2Cl2 and washed with water. The organic layer was dried over MgSO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography eluting with hexane/CH2Cl2 (1:9) to give 0.809 g (60%) of the desired product which was carried into the next step without further purification. MS (DCI/NH3) m/z: 307.4 (M+H)+.

Workup

washwashed with water
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationthe filtrate concentrated under reduced pressure
customThe residue was purified by flash chromatography
washeluting with hexane/CH2Cl2 (1:9)

Sources & evidence

ORD record: ord-59f9fc2dcfa8497294e6fb5c7ec7b7fd
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320986B2

Reaction notes

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