Dimethylformamide → HCID 57485964, compound

HRID 860510Notes

Reaction equation

HRID 860510 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 aicd (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) followe 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 silicagel columnc hromatography (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-8f5a7daad17a4e61864393f8bd989cfa
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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