Triethylamine → [3,5-Bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)amine

HRID 17035

Reaction equation

HRID 17035 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH2:4]Br.[F:11][C:12]([F:26])([F:25])[C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)[CH2:16][NH2:17].C(N(CC)CC)C>C(Cl)Cl>[F:11][C:12]([F:25])([F:26])[C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=1)[CH2:16][NH:17][CH2:4][C:3]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzeneHCID 5210993,5-Bis(trifluoromethyl)benzylamine

Product 1

HCID 86615390[3,5-Bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-fluoro benzyl bromide (0.5 g, 1.86 mmol) and 3,5-bis(trifluoromethyl)benzylamine (0.45 g, 1.86 mmol) in methylene chloride (10 ml) at 0° C., triethyl amine (0.39 ml, 2.80 mmol) was added. The solution was slowly warmed to room temperature and stirred for 18 h. The solvent was removed under reduced pressure. The title compound was obtained by flash column chromatography using EtOAc/hexane (2:8) as the eluant. 1H NMR (CDCl3, 500 MHz) δ 7.88 (s, 2H), 7.80 (s, 1H), 7.53 (dd, J=8.8, 5.3 Hz, 1H), 7.18 (dd, J=9, 3.3 Hz, 1H), 6.91 (dt, J=8.5, 3.3 Hz, 1H), 3.98 (s, 2H), 3.90 (s, 2H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-516eede3611145079004275bdd66cbaf
Source dataset
uspto-grants-2010_06
Patent number
US07737295B2

Linked notes

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