1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → Tert-butyl 2-fluoro-6-iodobenzoate

HRID 1034443Notes

Reaction equation

HRID 1034443 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[C:17]=1C(O)=O>C1(C)C=CC=CC=1>[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[C:17]=1[C:6]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:5]

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine2×HCID 27333022-Fluoro-6-iodobenzoic acid

Product 1

HCID 19022805Tert-butyl 2-fluoro-6-iodobenzoateYield 125.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N,N-Dimethylformamide di-t-butyl acetal (3.8 ml, 3.2 g) was added to a stirred mixture of 2-fluoro-6-iodobenzoic acid (1.25 g) in toluene (25 ml). The mixture was then stirred at 90° for 4 h, allowed to stand at room temperature for 60 h before further dimethylformamide di-t-butyl acetal (1 ml, 0.85 g) was added and heating continued at 90° for 90 min. After cooling, the orange solution was washed with water (50 ml), brine (50 ml), 10% aqueous lithium chloride solution and 8% aqueous sodium bicarbonate solution (50 ml), dried and concentrated in vacuo-to afford an orange liquid (1.9 g). Purification by chromatography eluting with System A (1:1) gave the title compound (1.37 g) as an orange liquid.

Workup

  1. additionwas added
  2. temperatureheating
  3. waitcontinued at 90° for 90 min
  4. temperatureAfter cooling
  5. washthe orange solution was washed with water (50 ml), brine (50 ml), 10% aqueous lithium chloride solution and 8% aqueous sodium bicarbonate solution (50 ml)
  6. customdried
  7. concentrationconcentrated in vacuo-to

Sources & evidence

ORD record
ord-31f9fc0b762146bb9c69f6d97c07e220
Source dataset
uspto-grants-1994_05
Patent number
US05317023

Reaction notes

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