Triethylamine → 2-(2-Nitrophenyl)propyl chloroformate

HRID 658513Notes

Reaction equation

HRID 658513 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH3:13])[CH2:11][OH:12])([O-:3])=[O:2].C(N(CC)CC)C.O=C(Cl)[O:23][C:24](Cl)(Cl)[Cl:25]>O1CCCC1>[Cl:25][C:24]([O:12][CH2:11][CH:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:13])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 113897552-(2-Nitrophenyl)propan-1-ol

Product 1

HCID 114479052-(2-Nitrophenyl)propyl chloroformateYield 130%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-nitrophenyl)propanol (16.12 g, 89 mmol) and triethylamine (12.4 mL, 89 mmol) in anhydrous tetrahydrofuran (THF) (96 mL) was added to a cold solution (0° C.) of diphosgene (10.7 mL, 89 mmol) in anhydrous THF (40 mL) over a period of 15 min with stirring and under nitrogen. After 30 min the cooling bath was removed and stirring was continued at room temperature for 3 h. The mixture was filtered and washed with THF. The solvent was removed in vacuo to give 28.20 g of 2-(2-nitrophenyl)propyl chloroformate as light brown oil that was directly used for the next reaction step. TLC: 20% ethyl acetate in hexanes, Rf=0.66.

Workup

  1. customAfter 30 min the cooling bath was removed
  2. stirringstirring
  3. filtrationThe mixture was filtered
  4. washwashed with THF
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-58943d3abc68468ab4521f82bd5246e6
Source dataset
uspto-grants-2011_12
Patent number
US08076501B2

Reaction notes

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