4-(Bromomethyl)benzoic acid → HCID 57762815, compound

HRID 230620Notes

Reaction equation

HRID 230620 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCl>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:9])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 225994-(Bromomethyl)benzoic acidHCID 31268PyrrolidineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 57762815HCID 57762815, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(bromomethyl)benzoic acid (2.43 g, 11.3 mmol) in dichloromethane (40 ml) was treated in one portion with solid 1,1′-carbonyldiimidazole (1.83 g, 11.3 mmol). This mixture was allowed to stir at room temperature for 15 minutes. Pyrrolidine (0.8 g, 11.3 mmol) was then added and the stirring continued for 1 hour at room temperature. The reaction mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate and evaporated in vaccuo (i.e under reduced pressure) to give a yellow oil which was added to a 20 g pre-packed silica column and eluted from 20-50% ethyl acetate in petroleum ether to give the title compound as a colourless solid (0.5 g, 17%).

Workup

  1. waitthe stirring continued for 1 hour at room temperature
  2. customThe reaction mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated in vaccuo (i.e under reduced pressure)
  5. customto give a yellow oil which
  6. additionwas added to a 20 g pre-packed silica column
  7. washeluted from 20-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0d35915178004d93909c8ec7e867d8a1
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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