Hydrochloric Acid → 3,5-Difluoro-4'-hydroxystilbene

HRID 78879Notes

Reaction equation

HRID 78879 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17]C(=O)C)=[CH:13][CH:12]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl>CO.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 687421603,5-Difluoro-4'-acetoxystilbene

Product 1

HCID 687420283,5-Difluoro-4'-hydroxystilbeneYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3,5-difluoro-4′-acetoxystilbene (0.69 g, 2.5 mmol) in MeOH (10 ml) was added 5 mL 4M HCl in 1,4-dioxane. The mixture was stirred for 20 minutes at ambient temperature. After purification by flash column, 3,5-difluoro-4′-hydroxystilbene (0.51 g, 88%) was obtained. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.40 (m, 2H), 7.05-6.83 (m, 6H), 6.67 (tt, 1H), 4.88 (s, 1H); 13C NMR (CDCl3, 75 MHz) δ 164.49 (d), 162.47, 156.01, 141.29, 130.90, 128.53, 124.74, 115.96, 109.03 (t), 102.53 (t); 19F NMR (CDCl3, 282 MHz) δ −31278.95 (t, J=1720.2 Hz); HRMS (EI+) found 232.0715 M+, calcd 232.0700 for C14H10F2O.

Workup

  1. customAfter purification by flash column

Sources & evidence

ORD record
ord-5da9b0dea3a0456eb2fbf4b946350d28
Source dataset
uspto-grants-2014_09
Patent number
US08841477B2

Reaction notes

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