Dimethylformamide → HCID 57485964, compound

HRID 2250655Notes

Reaction equation

HRID 2250655 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([OH:7])=O.CN(C)[CH:14]=[O:15].[C:17](Cl)(=O)[C:18](Cl)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([O:15][CH2:14][C:18]1[CH:17]=[CH:9][CH:10]=[CH:2][CH:3]=1)=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 57485964HCID 57485964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-bromo-5-iodobenzoic acid (5.00 g) and N,N-dimethylformamide (0.059 mL) in dichloromethane (50 mL) was added oxalyl chloride (1.47 mL) in an ice bath under a nitrogen atmosphere. After stirring for 1 hour, the volatile was evaporated off. The residue was dissolved in dichloromethane (50 mL), and to the solution was added bensyl alcohol (1.82 g) followed by triethyl amine (3.2 mL) in the ice bath. The mixture was stirred for 2 hours at room temperature. The mixture was partitioned between EtOAc and water. The organic layer was washed with water (two times), satd. NaHCO3, and brine, dried over MgSO4 and evaporated. Flash silica gel column chromatography (EtOAc-hexanes=1/200 to 20/200) afforded benzyl 3-bromo-5-iodobenzoate as white crystals (5.95 g).

Workup

  1. customthe volatile was evaporated off
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. additionto the solution was added bensyl alcohol (1.82 g)
  4. stirringThe mixture was stirred for 2 hours at room temperature
  5. customThe mixture was partitioned between EtOAc and water
  6. washThe organic layer was washed with water (two times)
  7. dry with materialNaHCO3, and brine, dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-ecdfdc1f5d294478b91e8e16092baff1
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

Loading…