Bromoacetyl bromide → HCID 13457739, compound

HRID 280120Notes

Reaction equation

HRID 280120 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].Br.[C:7]([C:15]1[N:16]([NH:20][CH3:21])[CH:17]=[CH:18][CH:19]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:21][N:20]([N:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:3](=[O:4])[CH2:2][Br:1]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 13457738HCID 13457738, compound

Product 1

HCID 13457739HCID 13457739, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromoacetyl bromide (8.47 g, 42 mmol) in 30 ml of dichloromethane was added over 30 minutes to a stirred slurry containing 2-benzoyl-1-methylaminopyrrole hydrobromide (14.9 g, 54.7 mmol) and sodium bicarbonate (5.9 g, 71 mmol) in 150 ml of dichloromethane. After 22 hours at room temperature the mixture was quenched with 150 ml of crushed ice and the layers were separated. The organic layer was washed with water, dried over anhydrous MgSO4, filtered and evaporated. The residual oil was flash chromatographed (silica gel, 5% hexane-ethyl acetate) to give 11.0 g (98%) of crystals, m.p. 76°-78°. A 2.2 g portion of this material was recrystallized from ether-hexane to afford 2.1 g of cubes, m.p. 76°-78°.

Workup

  1. customAfter 22 hours at room temperature the mixture was quenched with 150 ml of crushed ice
  2. customthe layers were separated
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed (silica gel, 5% hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d5475fb2df4d4e07bdee9c5d61d4e60a
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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