3-Bromo-4-methoxybenzaldehyde → HCID 22662127, compound

HRID 920866Notes

Reaction equation

HRID 920866 reaction equation
C([O-])(=O)C(C)(C)C.[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Zn+])=[CH:11][CH:10]=1.Br[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:21]=[O:22]>>[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=2[O:26][CH3:27])[CH:21]=[O:22])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 986623-Bromo-4-methoxybenzaldehydeHCID 178447604HCID 178447604, compound

Product 1

HCID 22662127HCID 22662127, compoundYield 82%

Procedure

(4-Fluorobenzyl)zinc pivalate (11) shows a clean coupling reaction with 3-bromo-4-methoxybenzaldehyde (5m) and afford 3-(4-fluorobenzyl)-4-methoxybenzaldehyde (6s) in 82% yield without observance of any addition products towards the aldehyde functionality (entry 19).

Sources & evidence

ORD record
ord-9cac57c1984f4bb78908db25aecad9f1
Source dataset
uspto-grants-2016_03
Patent number
US09273070B2

Reaction notes

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