Hydrochloric Acid → HCID 118005931, compound

HRID 1049618Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH:8]=1)N.N([O-])=O.[Na+].O.[ClH:23]>[Cl-].[Na+].O.Cl[Cu]>[Cl:23][C:4]1[CH:6]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH:8]=[C:2]([I:1])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

8 (3.4 g, 9.9 mmol) was suspended in concentrated HCl (17 mL) at 0° C. and stirred for 30 min. After this period, a solution of NaNO2 in H2O (0.6 g in 9.2 mL, 19 mmol) was added dropwise. Then the resulting mixture was stirred for 1 h at room temperature. This solution was added over 30 min to a solution of CuCl (16.6 g, 40 mmol) in concentrated HCl (17.0 mL) at 65° C. After addition, the mixture was heated at 80° C. for 30 minutes. The mixture was allowed to cool to room temperature before addition of brine. The solution was extracted with ethyl acetate, dried over anhydrous MgSO4, evaporated by rotary evaporation, and purified by column chromatography to give 1-chloro-3-iodo-5-(2-methoxyphenoxy)benzene (9) (1.5 g, 42%). 1H NMR (400 MHz, CDCl3) δ 7.35 (t, J=1.6 Hz, 1H), 7.23-7.15 (m, 1H), 7.13 (dd, J=2.2, 1.4 Hz, 1H), 7.06-6.94 (m, 3H), 6.83 (t, J=2.0 Hz, 1H), 3.82 (d, J=4.5 Hz, 3H).

Workup

waitAfter this period
stirringThen the resulting mixture was stirred for 1 h at room temperature
additionAfter addition
extractionThe solution was extracted with ethyl acetate
dry with materialdried over anhydrous MgSO4
customevaporated by rotary evaporation
custompurified by column chromatography

Sources & evidence

ORD record: ord-56a7c78a00f349518dff50df5310c35b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382245B2

Reaction notes

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