Triethylamine → ethyl 3-bromo-4-chloro-5-methyl-1H-pyrrole-2-carboxylate

HRID 655752Notes

Reaction equation

HRID 655752 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:7][C:8]=1[CH3:9].CCN(CC)CC.OS([O-])=O.[Na+]>C(Cl)Cl>[Br:1][C:5]1[C:4]([Cl:3])=[C:8]([CH3:9])[NH:7][C:6]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 23665763Sodium BisulfiteHCID 66707189ethyl 4-chloro-5-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 66707680ethyl 3-bromo-4-chloro-5-methyl-1H-pyrrole-2-carboxylateYield 106.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (0.56 ml, 11 mmol) was added to a solution of 1 g (5.3 mmol) of ethyl 4-chloro-5-methyl-1H-pyrrole-2-carboxylate (WO2006087543) and 0.8 ml (5.7 mmol) Et3N in CH2Cl2. After stirring at room temperature for 2 h, aqueous NaHSO3 was added and the CH2Cl2 was removed and the aqueous residue was partitioned between water and EtOAc. The EtOAc layer was separated and washed with brine. The EtOAc layer was dried over anhydrous MgSO4, and the solvent was removed to give 1.5 g of the product as a solid. MS (ES) (MH+): 240 for C8H9BrClNO2; NMR (d6-DMSO): 1.3 (t, 3H), 2.2 (s, 3H), 4.2 (q, 2H), 12.3 (s, 1H).

Workup

  1. customthe CH2Cl2 was removed
  2. customthe aqueous residue was partitioned between water and EtOAc
  3. customThe EtOAc layer was separated
  4. washwashed with brine
  5. dry with materialThe EtOAc layer was dried over anhydrous MgSO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-f8c919a1364e42e788a071f2188cd9ef
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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