Ethyl Acetate → 1-(2-Bromo-4-ethylsulfonylphenoxy)-2,4-difluorobenzene

HRID 575702Notes

Reaction equation

HRID 575702 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.[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[OH:22].C([O-])([O-])=O.[Cs+].[Cs+].CC(=O)OCC>CS(C)=O>[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:22][C:16]1[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=1[F:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 585219752-Bromo-4-(ethylsulfonyl)-1-fluorobenzene

Product 1

HCID 1180217871-(2-Bromo-4-ethylsulfonylphenoxy)-2,4-difluorobenzeneYield 81.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-bromo-1-fluoro-4-ethylsulfonylbenzene (130 mg, 0.49 mmol), 2,4-difluorophenol (78 mg, 0.60 mmol) and Cs2CO3 (478 mg, 1.47 mmol) in DMSO (5 mL) were heated at 100° C. for 12 h. EA extractive work up gave the title compound (150 mg, yield: 80.5%) as a grey solid. 1H NMR (CDCl3, 400 MHz) δ 8.18 (d, J=2.0 Hz, 1H), δ 7.75 (dd, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.22-7.16 (m, 1H), 7.06-6.95 (m, 2H), 6.80 (d, J=8.8 Hz, 1H), 3.16 (q, J=7.2 Hz, 2H), 1.33 (t, J=7.6 Hz, 3H). LCMS: 395.8 (M+NH4)+.

Sources & evidence

ORD record
ord-97361e010d244c05b791b37eb6c74a08
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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