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

HRID 1948347Notes

Reaction equation

HRID 1948347 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-carboxylate2×

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 (Intermediate 7) 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 was separated and washed with brine. Drying (MgSO4) and removal of solvent gave 1.5 g of 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 was separated
  4. washwashed with brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent

Sources & evidence

ORD record
ord-526dac7ce5864486836c2638b844f95d
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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