Bromoacetyl bromide → HCID 13457766, compound

HRID 280138Notes

Reaction equation

HRID 280138 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[N:7]([NH:12][CH3:13])[C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:5].C(=O)(O)[O-].[Na+].[Br:23][CH2:24][C:25](Br)=[O:26]>ClCCl>[CH3:13][N:12]([N:7]1[C:8]([CH3:11])=[CH:9][CH:10]=[C:6]1[C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[Cl:1])[C:25](=[O:26])[CH2:24][Br:23]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 13457765HCID 13457765, compound

Product 1

HCID 13457766HCID 13457766, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred slurry of 2-(2-chlorobenzoyl)-1-methylamino-5-methylpyrrole (18.7 g, 75 mmol) and sodium bicarbonate (14.2 g, 170 mmol) in 100 ml of dichloromethane was treated with a solution of bromoacetyl bromide (15.2 g, 90 mmol) in 30 ml of dichloromethane over 30 minutes and stirred at room temperature ovrnight. The reaction mixture was quenched with 100 ml of H2O, separated, washed with H2O and brine, dried (MgSO4), filtered, and evaporated. The resultant oil was purified by HPLC (silica, 1:1 ethyl acetate-hexane) to give an oil which crystallized from ether to give 22.7 g (82%) of needles, m.p. 108°-109°.

Workup

  1. customThe reaction mixture was quenched with 100 ml of H2O
  2. customseparated
  3. washwashed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant oil was purified by HPLC (silica, 1:1 ethyl acetate-hexane)
  8. customto give an oil which
  9. customcrystallized from ether

Sources & evidence

ORD record
ord-abb1fb7b66c34f0b80b2eb5d6b968035
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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