4-Bromo-1H-pyrrole-2-carbaldehyde → 4-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-pyrrolecarboxaldehyde

HRID 1057962Notes

Reaction equation

HRID 1057962 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][C:3]1=2.Br[C:19]1[CH:20]=[C:21]([CH:24]=[O:25])[NH:22][CH:23]=1>>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:19]3[CH:20]=[C:21]([CH:24]=[O:25])[NH:22][CH:23]=3)[CH:5]=[CH:4][C:3]1=2

Participants

3

Reactant 2

HCID 5996274-Bromo-1H-pyrrole-2-carbaldehydeHCID 10353857(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid

Product 1

HCID 226346854-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-pyrrolecarboxaldehydeYield 21.7%

Procedure

In a similar manner to Example 3(b), by reaction of 5.9 g (25.6 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylboronic acid with 3.7 g (21.3 mmol) of 4-bromo-2-pyrrolecarboxaldehyde, 1.3 g (21.6%) of the expected product are obtained, with a melting point of 211-2° C.

Sources & evidence

ORD record
ord-5afe2b1299d84f3187b8a23dddf8f412
Source dataset
uspto-grants-2003_02
Patent number
US06515021B1

Reaction notes

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