Bromoacetyl chloride → HCID 21957677, compound

HRID 2213666Notes

Reaction equation

HRID 2213666 reaction equation
Cl([O-])(=O)(=O)=O.[NH:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]=[N+]1CCCC1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:21][CH2:22][C:23](Cl)=[O:24].C(=O)(O)[O-:27].[Na+]>ClC(Cl)C.CCOCC>[Br:21][CH2:22][C:23]([C:9]1[CH:8]=[C:7]([CH:11]=[O:27])[NH:6][CH:10]=1)=[O:24]

Participants

7

Reactant 4

HCID 89602Bromoacetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 12196692HCID 12196692, compound

Product 1

HCID 21957677HCID 21957677, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of a 1-(1H-pyrrol-2-ylmethylene)pyrrolidinium perchlorate salt (5.2 g) in dichloroethane (100 mL) was treated with aluminum chloride (1.93 g). The mixture was cooled to 0° C., and then treated with 2-bromoacetyl chloride (2.2 mL). After stirring overnight at 0° C., the mixture was poured over crushed ice. Ether (60 mL) and sodium bicarbonate (1.93 g) were added and the mixture was stirred until the ice completely melted. The resulting mixture was extracted with ether and concentrated to afford 4-(bromoacetyl)-2-pyrrolecarboxaldehyde (1.88 g).

Workup

  1. additionthe mixture was poured
  2. customover crushed ice
  3. extractionThe resulting mixture was extracted with ether
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e1c2009ca5e40ed87d4a861bd8794cb
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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