Trifluoroacetic acid → 5-(3,5-Bis(4-methylnaphthalen-1-yl)phenyl)-2H-tetrazole

HRID 1472786Notes

Reaction equation

HRID 1472786 reaction equation
C([N:14]1[N:18]=[N:17][C:16]([C:19]2[CH:24]=[C:23]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([CH3:35])=[CH:27][CH:26]=3)[CH:22]=[C:21]([C:36]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:39]([CH3:46])=[CH:38][CH:37]=3)[CH:20]=2)=[N:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>ClCCl>[CH3:46][C:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:36]([C:21]2[CH:20]=[C:19]([C:16]3[N:15]=[N:14][NH:18][N:17]=3)[CH:24]=[C:23]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([CH3:35])=[CH:27][CH:26]=3)[CH:22]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 682936402-Benzhydryl-5-(3,5-bis(4-methylnaphthalen-1-yl)phenyl)-2H-tetrazole

Product 1

HCID 682936175-(3,5-Bis(4-methylnaphthalen-1-yl)phenyl)-2H-tetrazoleYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Benzhydryl-5-(3,5-bis(4-methylnaphthalen-1-yl)phenyl)-2H-tetrazole (0.32 g, 0.54 mmol) was dissolved in dichloromethane (2 mL). Anisole (0.3 mL, 2.76 mmol) and TFA (1 mL) were added sequentially. The reaction was stirred overnight, and then concentrated. The residue was purified by flash chromatography (hexane:ethyl acetate:AcOH=30:10:1) to afford 0.22 g (95.5%) of product as a white solid, 1H NMR (DMSO, 500 MHz) δ 8.24 (d, J=1.55 Hz, 2H), 8.25 (d, J=8.15 Hz, 2H), 8.03 (d, J=8.20 Hz, 2H), 7.72 (s, 1H), 7.65 (t, J=7.58 Hz, 2H), 7.60 (t, J=7.44 Hz, 2H), 7.56 (d, J=7.15 Hz, 2H), 7.51 (d, J=7.29 Hz, 2H), 2.74 (s, 6H); 13C NMR (DMSO, 125 MHz) δ 141.58, 136.38, 134.51, 133.81, 132.43, 130.72, 127.15, 127.03, 126.51, 126.32, 126.11, 125.61, 124.76.19.21.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography (hexane:ethyl acetate:AcOH=30:10:1)

Sources & evidence

ORD record
ord-bca2be5401764108bbf6bedf1499f4f1
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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