Ethyl Bromide → 1-(3-Chloro-4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole

HRID 2375380Notes

Reaction equation

HRID 2375380 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:17][CH3:18]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:10]([CH3:15])=[CH:11][CH:12]=[C:13]2[CH3:14])[CH:5]=[CH:6][C:7]=1[O:8][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 6332Ethyl BromideHCID 27645522-chloro-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzenol

Product 1

HCID 692753471-(3-Chloro-4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole

Procedure

Using the general procedure outlined in EXAMPLE 1, 1-(3-chloro-4-hydroxyphenyl)-2,5-dimethylpyrrole (1.11 g, 5 mmol) and an excess of bromoethane (1.0 mL) reacted to give 1-(3-chloro-4-ethoxyphenyl)-2,5-dimethylpyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 7.27 (d, 1H), 7.08 (dd, 1H), 6.99 (dd, 1H), 5.89 (s, 2H), 4.18 (q, 2H), 2.04 (s, 6H), 1.53 (t, 3H); MS (ESI) 250 (M+H)+.

Sources & evidence

ORD record
ord-0b70ff3fe15c4116b5eb4116c4e3b36c
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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