Chloroform → 2-Chloropropan-2-yl (4-nitrophenyl) carbonate

HRID 367077Notes

Reaction equation

HRID 367077 reaction equation
[C:1](=[O:16])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[O:2][C:3]([CH3:5])=[CH2:4].C(Cl)(Cl)[Cl:18]>C(OCC)C>[C:1](=[O:16])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[O:2][C:3]([Cl:18])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 22271989Isopropenyl p-nitrophenyl carbonate

Product 1

HCID 214789692-Chloropropan-2-yl (4-nitrophenyl) carbonateYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

The isopropenyl carbonate from step 88a (7.5 g, 33.6 mmol) was dissolved in a mixture of ethyl ether (100 mL) and chloroform (100 mL). The mixture was cooled to 0° C. and then bubbled with HCl gas. After standing at room temperature for 16 hours the mixture was purged with nitrogen to remove the excess HCl, and the solvent was evaporated to give the title compound (8.0 g, 92%): 1H NMR (CDCl3, 300 MHz) δ 2.11 (s, 6H), 7.39-7.44 (m, 2H), 8.27-8.32 (m, 2H).

Workup

  1. custombubbled with HCl gas
  2. customthe mixture was purged with nitrogen
  3. customto remove the excess HCl
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-55592d9300194a44b0bace598ce4654d
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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