1,2,4-Trimethoxybenzene → HCID 178493536, compound

HRID 591374Notes

Reaction equation

HRID 591374 reaction equation
F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]#[N:15])=[CH:10][CH:9]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[O:30][CH3:31]>C(O)C>[CH3:29][O:28][C:25]1[CH:24]=[C:23]([O:30][CH3:31])[C:22]([O:21][CH3:20])=[CH:27][C:26]=1/[N:15]=[N:14]/[C:11]1[CH:12]=[CH:13][C:8]([S:7]([F:16])([F:17])([F:18])([F:19])[F:6])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 672841,2,4-TrimethoxybenzeneHCID 1222352751605274-62-1

Product 1

HCID 178493536HCID 178493536, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diazonium salt 1 (14.1 mg, 0.0443 mmol) and 1,2,4-trimethoxybenzene (15.6 mg, 0.0928 mmol) were dissolved in 0.148 g of 95% aqueous ethanol. After 0.1 h, a red solid precipitated. After filtration the red solid was purified by SiO2 column chromatography (7:3 hexane/ethyl acetate) to give 27c as a red oil (12.8 mg, 72%): IR (ATR): {tilde over (v)}=2941, 1607, 1598, 1505, 1472, 1436, 1269, 1209, 1126, 1093, 1030, 839, 824 cm−1. MS (GC, EI): m/z=398 [M+], 140, 110. 1H NMR (500 MHz, CDCl3): δ=7.91 (d, J=9.0 Hz, 2H), 7.86 (d, J=9.0 Hz, 2H), 7.44 (s, 1H), 6.64 (s, 1H), 4.07 (s, 3H), 4.01 (s, 3H), 3.93 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=154.74 (C), 154.70 (C), 154.3 (C), 154.0 (C), 144.1 (C), 135.1 (C), 126.9 (2CH), 122.4 (2CH), 98.8 (CH), 97.5 (CH), 57.6 (CH3), 56.22 (CH3), 56.17 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=84.4 (quint, J=150 Hz, 1 F), 63.3 (d, J=150 Hz, 4 F) ppm.

Workup

  1. customa red solid precipitated
  2. filtrationAfter filtration the red solid
  3. customwas purified by SiO2 column chromatography (7:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fe99099c59b348efb753f63802a69101
Source dataset
uspto-grants-2016_01
Patent number
US09238660B1

Reaction notes

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