Ethyl bromoacetate → HCID 22156057, compound

HRID 1897534Notes

Reaction equation

HRID 1897534 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[Br:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]>ClCCl>[Br-:8].[CH2:13]([O:12][C:10](=[O:11])[CH2:9][N+:2]1([CH3:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1)[CH3:14]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 79724-Methylmorpholine

Product 1

HCID 22156057HCID 22156057, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3.0 g (29.6 mmol) of 4-methylmorpholine was dissolved in 50 mL dichloromethane and cooled to 0° C. in an ice bath. To this solution 5.0 g of ethyl bromoacetate (29.6 mmol) was added dropwise with continuous stirring and the mixture was then allowed to warm to room temperature. The clear solution started to form white precipitate after 5 minutes of stirring at room temperature. The resulting mixture was stirred for another 3 h. The precipitate was isolated by vacuum filtration using a 30 mL glass fritted funnel and washed 3 times with 30 mL of acetone to give 8.0 g of the product as a white solid. Positive mode ESI/MS: m/z=188 (M+, minus Br); confirmed by 1H NMR.

Workup

  1. temperatureto warm to room temperature
  2. customto form white precipitate after 5 minutes
  3. stirringof stirring at room temperature
  4. stirringThe resulting mixture was stirred for another 3 h
  5. customThe precipitate was isolated by vacuum filtration
  6. washwashed 3 times with 30 mL of acetone

Sources & evidence

ORD record
ord-bb2f147ac97749a887eb631790bdc37f
Source dataset
uspto-grants-2013_08
Patent number
US08519125B2

Reaction notes

Loading…