Methyl chloroformate → Methyl (4-fluoro-3-nitrophenyl)carbamate

HRID 1987189Notes

Reaction equation

HRID 1987189 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[F:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15].CCN(C(C)C)C(C)C>ClCCl>[F:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:2](=[O:3])[O:4][CH3:5])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 677684-Fluoro-3-nitroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 3636899Methyl (4-fluoro-3-nitrophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl chloroformate (13.2 mL, 170.2 mmol) was added dropwise to a cold (0° C.) dichloromethane (200 mL) solution of 4-fluoro-3-nitro aniline (24.15 g, 154.7 mmol) and DIPEA (35 mL, 201 mmol). The reaction mixture was stirred at rt overnight. The solution was then diluted with 200 mL of dichloromethane and washed with 2M HCl, brine and dried over anhydrous MgSO4. The solvent was concentrated and the product was directly used for the next step without further purification. Yield: 35.5 g (99%). 1H NMR (400 MHz, CHLOROFORM-D) δ 3.81 (s, 3H), 7.02 (s, 1H), 7.23 (m, 1H), 7.72 (d, J=8.59 Hz, 1H), 8.17 (dd, J=6.35, 2.64 Hz, 1H).

Workup

  1. washwashed with 2M HCl, brine
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationThe solvent was concentrated
  4. customthe product was directly used for the next step without further purification

Sources & evidence

ORD record
ord-9c6e0c5c68cc413688d2ccb75624b075
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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