Water → 2-Bromo-4-ethylsulfonyl-1-methoxybenzene

HRID 575572Notes

Reaction equation

HRID 575572 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.C[O-].[Na+].O.[C:18](OCC)(=[O:20])C>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:20][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 10942334Sodium MethoxideHCID 585219752-Bromo-4-(ethylsulfonyl)-1-fluorobenzene

Product 1

HCID 109788092-Bromo-4-ethylsulfonyl-1-methoxybenzeneYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-bromo-4-ethylsulfonyl-1-fluorobenzene (0.6 g, 2.25 mmol) and sodium methoxide (1.2 g, 22.2 mmol) in THF (20 mL) was stirred at room temperature for 18 h. Water (30 mL) was added and extractive work up with ethyl acetate followed by silica gel chromatography (PE:EA=10:1 to 1:1) gave the title compound (0.5 g, 79.4%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.08 (d, J=2.4 Hz, 1H), 7.87-7.84 (dd, J1=8.6 Hz, J2=2.4 Hz, 1H), 7.04 (d, J=8.8 Hz, 1H), 3.99 (s, 3H), 3.11 (q, J=7.4 Hz, 2H), 1.30 (t, J=7.4 Hz, 3H).

Sources & evidence

ORD record
ord-3cda75486fe04705801011bde5015c66
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

Loading…