Hydrogen Bromide → HCID 67121893, compound

HRID 1518672Notes

Reaction equation

HRID 1518672 reaction equation
S(=O)(=O)(O)O.[BrH:6].[CH3:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:11]=[C:10]([CH3:22])[C:9]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29]O)[CH:24]=1>O>[Br:6][CH2:29][C:25]1[CH:24]=[C:23]([C:9]2[C:8]([CH3:7])=[CH:13][C:12]([O:14][CH2:15][CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:11][C:10]=2[CH3:22])[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 1118Sulfuric AcidHCID 593425562',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)(1,1'-biphenyl)-3-methanol

Product 1

HCID 67121893HCID 67121893, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Concentrated sulfuric acid (1.4 g) was added dropwise to 48% hydrobromic acid (15 ml) at room temperature and [2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]-[1,1′-biphenyl]-3-yl]methanol (25 g) synthesized in accordance with the method described in [WO 2008/001931 pamphlet] was divided into five portions and added to the mixture. The reaction mixture was stirred at 60° C. for 2.5 hours and 48% hydrobromic acid (3.3 ml) was added to the mixture. The mixture was further stirred for 1 hour at the same temperature. After the reaction mixture was allowed to cool, water was added to the reaction mixture. The mixture was extracted with ethyl acetate. The obtained organic phase was washed with water, then washed with brine, and dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure to give the title compound (27 g) as a pale yellow solid.

Workup

  1. additionadded to the mixture
  2. stirringThe mixture was further stirred for 1 hour at the same temperature
  3. temperatureto cool
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe obtained organic phase was washed with water
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationFrom the organic phase, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a9114d4bdf674658873b68ffc3eb0471
Source dataset
uspto-grants-2015_07
Patent number
US09072758B2

Reaction notes

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