4-Bromobenzaldehyde → 4'-But-2-ynoylbiphenyl-4-carbaldehyde

HRID 717671Notes

Reaction equation

HRID 717671 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1.Br[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.OCC1SC(B(O)O)=CC=1>>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)=[CH:3][CH:4]=1)(=[O:12])[C:9]#[C:10][CH3:11]

Participants

4

Reactant 3

HCID 707414-BromobenzaldehydeHCID 43742655-Hydroxymethylthiophene-2-boronic acidHCID 666150711-(4-Bromophenyl)but-2-yn-1-one

Product 1

HCID 866606164'-But-2-ynoylbiphenyl-4-carbaldehydeYield 58%

Procedure

When the product of Step A and 4-carbaldehyde-boronic acid were substituted for 4-bromobenzaldehyde and 5-(hydroxymethyl)thiophen-2-ylboronic acid, respectively, in Example 22, Step A, the similar procedure afforded the title compound in 58% yield, as a creamy gum. 1H-NMR (CDCl3) 10.07 (s, 1H); 8.23 (d, 2H, J=8.4 Hz); 7.98 (d, 2H, J=8.4 Hz); 7.78 (d, 2H, J=8.24 Hz); 7.72 (d, 2H, J=8.54 Hz); 2.18 (s, 3H).

Sources & evidence

ORD record
ord-99b60aa90a9a4ff8b8a60efbb5cbd651
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

Loading…