(4-Methoxyphenyl)boronic acid → Methyl 5-(4-methoxyphenyl)thiophene-2-carboxylate

HRID 1853933Notes

Reaction equation

HRID 1853933 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:14]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 605713Methyl 5-bromothiophene-2-carboxylate

Product 1

HCID 5150032Methyl 5-(4-methoxyphenyl)thiophene-2-carboxylateYield 62.6%

Procedure

Following General Procedure B, 4-methoxyphenylboronic acid (2.7 g, 18 mmol) was reacted with methyl 5-bromothiophene-2-carboxylate (2.0 g, 9.0 mmol) to afford the desired product (1.4 g, 61%): 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=3.9 Hz, 1H), 7.53 (td, J=9.7, 2.5 Hz, 2H), 7.14 (d, J=3.9 Hz, 1H), 6.89 (td, J=9.7, 2.5 Hz, 2H), 3.87 (s, 3H), 3.80 (s, 3H).

Sources & evidence

ORD record
ord-e311bc9fe328485d91c411ccd82571b2
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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