Benzyl Bromide → HCID 8543774, compound

HRID 1636159Notes

Reaction equation

HRID 1636159 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].C(N(CC)CC)C.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:7][C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 12473Pyrrole-2-Carboxylic Acid

Product 1

HCID 8543774HCID 8543774, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lit. J. Org. Chem., 44:975 (1979). To a stirred solution of 5.0 g (45.0 mmol) pyrrole-2-carboxylic acid and 31.3 ml (225 mmol) triethylamine in 100 ml DMF was added dropwise 26 ml (225 mmol) benzyl bromide and stirring continued for 72 h at room temperature. The reaction mixture was then concentrated in vacuo and the residue resuspended in dichloromethane and washed twice with saturated sodium bicarbonate solution and twice with water, and the aqueous phases back-extracted with dichloromethane. The combined organic extracts were dried over sodium sulphate and concentrated in vacuo. Flash chromatography (25% EtOAc in hexane) afforded 8.23 g (90%) of the title compound as a yellow oil. MS m/e (%): 201 (M+, 33), 94 ([M−OBn]+, 22), 91 (Bn+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washwashed twice with saturated sodium bicarbonate solution and twice with water
  3. extractionthe aqueous phases back-extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6a28e512e0a49dbbb66bffa9d4c000e
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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