Benzyl Bromide → benzyl 3-chloro-1H-pyrrole-2-carboxylate

HRID 524983Notes

Reaction equation

HRID 524983 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([OH:9])=[O:8].C(N(CC)CC)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[Cl:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 221800183-chloro-1H-pyrrole-2-carboxylic acid

Product 1

HCID 70922227benzyl 3-chloro-1H-pyrrole-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-1H-pyrrole-2-carboxylic acid (15 g, 0.1 mol) in N,N-dimethylformamide (300 mL) and triethylamine (72 mL, 0.52 mmol) under argon atmosphere was added benzyl bromide (61 mL, 0.52 mmol) at 0-5° C. and the reaction was stirred mechanically overnight at room temperature. Next day, the reaction mixture was concentrated in vacuum and the residue was suspended in 4% aqueous solution of sodium bicarbonate (300 mL) and extracted with ethyl acetate (2×250 mL). The organic layers were mixed and washed with more 4% aqueous solution of sodium bicarbonate, water and brine, and were dried (magnesium sulphate, MgSO4) and concentrated under reduced pressure to give 21.4 g of a residue corresponding to the title compound (88% yield).

Workup

  1. concentrationNext day, the reaction mixture was concentrated in vacuum
  2. extractionextracted with ethyl acetate (2×250 mL)
  3. additionThe organic layers were mixed
  4. washwashed with more 4% aqueous solution of sodium bicarbonate, water and brine
  5. dry with materialwere dried (magnesium sulphate, MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd085c4174ed4cdea2cb6a09c109b59c
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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