Methyl chloroformate → Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)carbamate

HRID 217484Notes

Reaction equation

HRID 217484 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[Br:18].Cl[C:29]([O:31][CH3:32])=[O:30].C(N(CC)CC)C>C(Cl)Cl>[F:23][C:22]([F:25])([F:24])[C:20]1[CH:19]=[C:5]([CH:4]=[C:3]([C:2]([F:26])([F:1])[F:27])[CH:21]=1)[CH2:6][N:7]([CH2:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[Br:18])[C:29](=[O:30])[O:31][CH3:32]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 86615393[3,5-Bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)amine

Product 1

HCID 86615394Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-nitrobenzyl)amine from Step C (0.47 g, 1.0 mmol) in methylene chloride (20 ml) at room temperature, methyl chloroformate (0.12 ml, 1.54 mmol) and triethylamine (0.29 ml, 2.05 mmol) were added. The solution was stirred at room temperature for 18 h. The solvent was removed under reduced pressure. The title compound was obtained by flash column chromatography using 1:9 EtOAc/hexane as the eluant. 1H NMR (CDCl3, 500 MHz) δ 8.11 (m, 1H), 8.02 (dd, J=9.0, 2.5 Hz, 1H), 7.81 (s, 1H), 7.74 (d, J=9.0 Hz, 1H), 7.70 (m, 1H), 7.65 (m, 1H), 4.67 (m, 4H), 3.89 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6c88d3264761449c8881c8459c370794
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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