4-Bromo-1H-pyrrole-2-carbaldehyde → 4-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-2-pyrrolecarboxaldehyde

HRID 1057965Notes

Reaction equation

HRID 1057965 reaction equation
[CH3:1][C:2]1[C:3](B(O)O)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.Br[C:20]1[CH:21]=[C:22]([CH:25]=[O:26])[NH:23][CH:24]=1>>[CH3:1][C:2]1[C:3]([C:20]2[CH:21]=[C:22]([CH:25]=[O:26])[NH:23][CH:24]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 5996274-Bromo-1H-pyrrole-2-carbaldehydeHCID 10037535(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid

Product 1

HCID 221315074-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-2-pyrrolecarboxaldehyde

Procedure

In a similar manner to Example 3(b), by reaction of 2.47 g (10 mmol) of 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid with 1.5 g (8.4 mmol) of 4-bromo-2-pyrrolecarboxaldehyde, 950 mg (38.5%) of the expected aldehyde are obtained, with a melting point of 128-9° C.

Workup

  1. customare obtained, with a melting point of 128-9° C.

Sources & evidence

ORD record
ord-f83c28d142ff4d2a9ebdbfabce4636e6
Source dataset
uspto-grants-2003_02
Patent number
US06515021B1

Reaction notes

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