4-Bromo-2-methylbenzaldehyde → 2-Methyl-4-butylbenzaldehyde

Reaction equation

[CH3:1][C:2]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11]([B-](F)(F)F)[CH2:12][CH2:13][CH3:14].[K+]>>[CH3:1][C:2]1[CH:9]=[C:8]([CH2:11][CH2:12][CH2:13][CH3:14])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

Reactant 2

HCID 135551504-Bromo-2-methylbenzaldehyde

HCID 23693579Potassium Butyltrifluoroborate

Product 1

HCID 1182289742-Methyl-4-butylbenzaldehydeYield 35%

Procedure

The compound was synthesized as in Example 3.1 using 2-methyl-4-bromobenzaldehyde (113 mg, 0.57 mmol) in place of 5-bromo-2-formylfuran and potassium butyltrifluoroborate (113 mg, 0.69 mmol) in place of hexylboronic acid to give 2-methyl-4-butylbenzaldehyde (34 mg, 35%). Used without further characterization.

Sources & evidence

ORD record: ord-eb46a0acf6184148b18cb68e5587639e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315495B2

Reaction notes

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