4-Bromo-2,6-difluorobenzaldehyde → HCID 86658839, compound

HRID 447567Notes

Reaction equation

HRID 447567 reaction equation
Br[C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH:6]=[O:7])=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]1([CH3:22])[C:17]([CH3:19])([CH3:18])[O:16][B:15]([CH:20]=[CH2:21])[O:14]1>>[F:10][C:8]1[CH:9]=[C:2](/[CH:21]=[CH:20]/[B:15]2[O:16][C:17]([CH3:19])([CH3:18])[C:13]([CH3:22])([CH3:12])[O:14]2)[CH:3]=[C:4]([F:11])[C:5]=1[CH:6]=[O:7]

Participants

3

Reactant 2

HCID 27732904-Bromo-2,6-difluorobenzaldehydeHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86658839HCID 86658839, compoundYield 76%

Procedure

According to procedure for the synthesis of example A51A, by using 4-bromo-2,6-difluorobenzaldehyde (1.10 g, 4.98 mmol) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.97 mL, 5.72 mmol) to give the title compound as a colorless oil (1.10 g, 76%). 1H NMR (400 MHz, CDCl3) δ 10.31 (s, 1H), 7.05 (d, J=9.6 Hz, 2H), 7.22 (d, J=8.8 Hz, 1H), 6.28 (d, J=18.8 Hz, 1H), 1.33 (s, 12H); MS ESI 295.1 [M+H]+, calcd for [C15H17BF2O3+H]+ 295.13.

Sources & evidence

ORD record
ord-eac563b30eec46ba9a9046c38fb40b5f
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Reaction notes

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