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

HRID 17036Notes

Reaction equation

HRID 17036 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[Br:16].Cl[C:27]([O:29][CH3:30])=[O:28].C(N(CC)CC)C>C(Cl)Cl>[F:23][C:20]([F:21])([F:22])[C:18]1[CH:17]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:19]=1)[CH2:6][N:7]([CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[Br:16])[C:27](=[O:28])[O:29][CH3:30]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 86615390[3,5-Bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)amine

Product 1

HCID 86615391Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)amine from Step A (0.14 g) in methylene chloride at room temperature, excess methyl chloroformate (0.1 ml) and triethyl amine (0.1 ml) were added. The solution was stirred at room temperature for 2 h and the solvent was removed under reduced pressure. The title compound was obtained by flash column chromatography using EtOAc/hexane (1:9) as the eluant. 1H NMR (CDCl3, 500 MHz) δ 7.80 (s, 1H), 7.68 (s, 1H), 7.60 (s, 1H), 7.48 (m, 1H), 6.88 (m, 2H), 4.60 (m, 4H), 3.81 (s, 3H).

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2e68953b859f4d4987dd68f6bb98408c
Source dataset
uspto-grants-2010_06
Patent number
US07737295B2

Reaction notes

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