1-(Azidomethyl)-3-(trifluoromethyl)benzene → HCID 44517958, compound

HRID 1424681Notes

Reaction equation

HRID 1424681 reaction equation
[I:1][C:2]#[C:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][CH3:15].[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[CH2:21][N:22]=[N+:23]=[N-:24]>>[I:1][C:2]1[N:22]([CH2:21][C:20]2[CH:25]=[CH:26][CH:27]=[C:18]([C:17]([F:16])([F:29])[F:28])[CH:19]=2)[N:23]=[N:24][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][CH3:15]

Participants

3

Reactant 2

HCID 212826681-(Azidomethyl)-3-(trifluoromethyl)benzeneHCID 44517957HCID 44517957, compound

Product 1

HCID 44517958HCID 44517958, compound

Procedure

Synthesized from 4-(3-iodoprop-2-ynyloxy)-3-methoxybenzaldehyde and 3-trifluoromethyl-benzylazide using general procedure; 0.398 g, 0.769 mmol, 97%; mp=130-134° C. (dec.); IR (υ[cm−1]) 3123, 1702, 1689, 1588, 1506, 1329, 1262, 1133, 1123, 994, 792; 1H NMR (600 MHz, CDCl3) δ=9.83 (s, 1H), 7.59 (d, J=7.6, 1H), 7.56 (s, 1H), 7.47 (t, J=7.7, 1H), 7.41 (dd, J=15.8, 6.7, 2H), 7.39 (s, 1H), 7.21 (d, J=8.1, 1H), 5.62 (s, 2H), 5.27 (s, 2H), 3.88 (s, 3H); 13C NMR (151 MHz, CDCl3) δ=191.2, 153.1, 150.5, 147.5, 135.0, 131.6, 131.6 (q, J=32.7), 131.1, 129.9, 126.7, 125.9 (q, J=3.6), 125.1 (q, J=3.7), 123.9 (q, J=272.4), 113.5, 109.7, 81.2, 62.9, 56.3, 54.0; HRMS (ESI-TOF) (m/z): [M+H]+ calcd for C19H16F3IN3O3, 518.0183; found 518.0186.

Sources & evidence

ORD record
ord-c5b722cd0aee41e68ea4b315790b4fe7
Source dataset
uspto-grants-2015_01
Patent number
US08927736B2

Reaction notes

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