Water → 1-Bromo-4-fluoro-2-methoxy-5-(methylsulfonylmethyl)benzene

HRID 575583Notes

Reaction equation

HRID 575583 reaction equation
[OH:1]OS([O-])=O.[K+].[Br:7][C:8]1[CH:13]=[C:12]([CH2:14][S:15][CH3:16])[C:11]([F:17])=[CH:10][C:9]=1[O:18][CH3:19].[OH2:20]>CO>[Br:7][C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:16])(=[O:1])=[O:20])[C:11]([F:17])=[CH:10][C:9]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 1180222021-Bromo-4-fluoro-2-methoxy-5-(methylsulfanylmethyl)benzene

Product 1

HCID 1180225411-Bromo-4-fluoro-2-methoxy-5-(methylsulfonylmethyl)benzeneYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Oxone (20.9 g, 34.1 mmol) in H2O (100 mL) was added drop-wise to a solution of 1-bromo-4-fluoro-2-methoxy-5-(methylsulfanylmethyl)benzene (4.3 g, 16.2 mmol) in MeOH (100 mL) at 0° C. The mixture was then stirred at room temperature for 3 h and then poured into water. Extractive work up with ethyl acetate, washing with saturated aqueous Na2SO3 (40 mL) and brine, gave a solid that was triturated with 1:10/EA:MTBE to give the title compound (4.40 g, 93.0%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.66 (d, J=8.0 Hz, 1H), 6.72 (d, J=11.2 Hz, 1H), 4.22 (s, 2H), 3.92 (s, 3H), 2.83 (s, 3H). LCMS: 318.9 (M+Na)+

Workup

  1. washExtractive work up with ethyl acetate, washing with saturated aqueous Na2SO3 (40 mL) and brine
  2. customgave a solid
  3. customthat was triturated with 1:10/EA

Sources & evidence

ORD record
ord-0141195e6dac4df79a714513c671b9d4
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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