Diethyl Ether → 1-Chloro-3-ethenyl-2-[(propan-2-yl)oxy]benzene

HRID 554697Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH2:9])[C:3]=1[OH:10].[C:11]([O-])([O-])=O.[K+].[K+].CCO[CH2:20][CH3:21]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH2:9])[C:3]=1[O:10][CH:20]([CH3:21])[CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

2-chloro-6-vinylphenol (1.55 g, 10 mmol) and 2-iodopropance (1.5 ml, 15 mmol, 1.5 equiv) were dissolved in DMF, followed by adding K2CO3 (3.9 g, 30 mmol) into DMF solution, then heated at 60° C. overnight. etherification was monitored by TLC and HPLC until completed. The mixture was diluted with Et2O (250 mL), and washed with water (2×200 mL). The aqueous layer was extracted twice with Et2O (150 mL), and the combined organic layers were washed with brine, and dried over MgSO4. The product was purified by flash column (Hexanes:Et2O=6:1) to offer 1.69 g of product 4a (Yield: 82%, purity: 98%). 1HNMR (CDCl3: δ=7.26 ppm): 7.42 (dd, 1H, J=1.56, 7.82 Hz), 7.29 (dd, 1H, J=1.56, 7.83 Hz), 7.02 (m, 2H), 5.73 (d, 1H, J=17.60 Hz), 5.56 (d, 1H, J=11.34 Hz), 4.43 (m, 1H), 1.32 (d, 6H, J=6.26 Hz). (M+H+): m/z calculated: 197.1, found: 197.1.

Workup

washwashed with water (2×200 mL)
extractionThe aqueous layer was extracted twice with Et2O (150 mL)
washthe combined organic layers were washed with brine
dry with materialdried over MgSO4
customThe product was purified by flash column (Hexanes:Et2O=6:1)

Sources & evidence

ORD record: ord-23183610a29a4f3eac191103a618ffd5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049025B2

Reaction notes

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