Potassium Carbonate → 5-Bromo-2-(2-pyrrolidin-1-ylethoxy)benzaldehyde

HRID 734837Notes

Reaction equation

HRID 734837 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].Cl[CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 816691-(2-Chloroethyl)pyrrolidine

Product 1

HCID 176209185-Bromo-2-(2-pyrrolidin-1-ylethoxy)benzaldehyde

Conditions

Temperature
75 °C

Procedure

A suspension of 6.00 g (29.85 mmol) of 5-bromo-2-hydroxybenzaldehyde, 5.84 g (3.43 mmol) of 1-(2-chloroethyl)pyrrolidine, and 12.38 g (89.54 mmol) of potassium carbonate was stirred for 2 hours at 50° C. and for 2 hours at 75° C., cooled to RT, filtered, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, gradient EtOAc/MeOH 100:0→85:15). Yield: 5.89 g (66% of theoretical); C13H16BrNO2 (M=298.176); calc.: molpeak (M+H)+: 298/300 (Br); found: molpeak (M+H)+: 298/300 (Br); HPLC-MS: 4.82 minutes (method A).

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. customevaporated down in vacuo
  4. customThe crude product was purified by column chromatography (silica gel, gradient EtOAc/MeOH 100:0→85:15)
  5. custom4.82 minutes (method A)

Sources & evidence

ORD record
ord-8f5f830c434b44ec8632c7f61206c674
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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