Sodium Thiosulfate → 2-Bromo-4-(ethylsulfonyl)-1-fluorobenzene

HRID 518300Notes

Reaction equation

HRID 518300 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](SCC)[CH:5]=[CH:4][C:3]=1[F:11].[CH:12]1C=C(Cl)C=C(C(OO)=O)[CH:13]=1.[O-:23][S:24]([O-:27])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([S:24]([CH2:12][CH3:13])(=[O:27])=[O:23])[CH:5]=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86704956(3-Bromo-4-fluorophenyl)(ethyl)sulfane

Product 1

HCID 585219752-Bromo-4-(ethylsulfonyl)-1-fluorobenzeneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-bromo-4-ethylsulfanyl-1-fluorobenzene (2.2 g, 9.36 mmol) in DCM (20 mL) was added m-CPBA (6.47 g, 37.4 mmol). The mixture was stirred at room temperature for 12 h. Aqueous saturated Na2S2O3 (100 mL) was added, and extractive work up with CH2Cl2 gave the title compound (1.5 g, 50%) as a yellow solid which was carried on without purification. 1H NMR (CDCl3, 400 MHz) δ 8.15 (dd, J1=6.4 Hz, J2=2.4 Hz, 1H), 7.88-7.85 (m, 1H), 7.32 (t, J=8.4 Hz, 1H), 3.14 (q, J=7.2 Hz, 2H), 1.31 (t, J=7.6 Hz, 3H).

Sources & evidence

ORD record
ord-c8d210d2c33f4505a36f586e6ce4a014
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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