Potassium Butyltrifluoroborate → Methyl-6-butylbenzofuran-2-carboxylate

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:8]=2[CH:9]=1)=[O:4].[CH2:15]([B-](F)(F)F)[CH2:16][CH2:17][CH3:18].[K+]>>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[C:12]([CH2:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:8]=2[CH:9]=1)=[O:4]

Participants

Reactant 2

HCID 23693579Potassium Butyltrifluoroborate

HCID 59015856Methyl 6-bromo-1-benzofuran-2-carboxylate

Product 1

HCID 118228973Methyl-6-butylbenzofuran-2-carboxylateYield 67%

Procedure

Methyl-6-butylbenzofuran-2-carboxylate was synthesized as in Example 3.1 using methyl-6-bromobenzofuran-2-carboxylate (195 mg, 0.76 mmol) in place of 5-bromo-2-formylfuran and potassium butyltrifluoroborate (188 mg, 1.15 mmol) in place of hexylboronic acid to give methyl-6-butylbenzofuran-2-carboxylate (118 mg, 67%). Used without further characterization.

Sources & evidence

ORD record: ord-63a809f89f9d40b985e6c741c53da17a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315495B2

Reaction notes

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