Dimethylformamide → Tert-butyl 2-iodobenzoate

HRID 425333Notes

Reaction equation

HRID 425333 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].I[C:12]1C=CC=[CH:17][C:13]=1[C:14](Cl)=O.C(Cl)(=O)C(Cl)=O.CN(C=O)C>C(Cl)Cl>[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:13]([CH3:17])([CH3:14])[CH3:12])=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 69412-Iodobenzoic acidHCID 65578Oxalyl chlorideHCID 691122-Iodobenzoyl chloride

Product 1

HCID 11438134Tert-butyl 2-iodobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Iodobenzoic acid (10.06 g, 40.56 mmol) was converted to 2-iodobenzoic chloride by reacting with oxalyl chloride (5.34 mL, 60.84 mmol) in methylene chloride (100 mL), initiated by a drop DMF. The solvent and excess oxalyl chloride were removed by rotary evaporation. To a 250 mL one neck round bottom flask was charged t-butanol with THF (50 mL) and then cooled to −78 C. A solution of n-butyl lithium in hexanes (2.5 M, 24.3 mL) was added, followed by the solution of 2-iodobenzoic chloride in THF (50 mL). The resulting reaction mixture was stirred at −78 C for 20 min and then at rt for 2 hours. The reaction was quenched by water and worked up. The product was purified by flash chromatography to afford the title compound as a white solid.

Workup

  1. customThe solvent and excess oxalyl chloride were removed by rotary evaporation
  2. additionTo a 250 mL one neck round bottom flask was charged t-butanol with THF (50 mL)
  3. temperaturecooled to −78 C
  4. additionA solution of n-butyl lithium in hexanes (2.5 M, 24.3 mL) was added
  5. customThe resulting reaction mixture
  6. waitat rt for 2 hours
  7. customThe reaction was quenched by water
  8. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-ef67f042de8046b4b489f90eb7e29d5e
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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