4-Bromo-2-fluorobenzaldehyde → 2-Fluoro-4-phenylbenzaldehyde

HRID 646722Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)CCC>C1(C)C=CC=CC=1.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>[F:10][C:4]1[CH:3]=[C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 4-bromo-2-fluorobenzaldehyde (0.15 g, 0.74 mmol), tributyl(phenyl)stannane (0.27 mL, 0.81 mmol) and Pd(PPh3)4 (0.043 g, 0.037 mmol) in PhCH3 (2.5 mL) was heated in a sealed reaction tube to 110° C. for 12 h. Additional tributyl(phenyl)stannane (0.20 mL, 0.61 mmol) and Pd(PPh3)4 (0.043 g, 0.037 mmol) were added and the solution was further heated to 110° C. for 2 h. The solvent was removed in vacuo. The residue was purified via column chromatography (SiO2, 5:1 hexanes/EtOAc) to provide 0.23 g (>100% yield) of 3-fluorobiphenyl-4-carbaldehyde, which was used without further purification: MS (EI) for C13H9OF: 201 (MH+).

Workup

customThe solvent was removed in vacuo
customThe residue was purified via column chromatography (SiO2, 5:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-0adb05e1e79c4c7d99e56146512afd55
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704995B2

Reaction notes

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