Sodium Hydroxide → 4-(2-Bromo-phenylsulfanyl)-3-sulfino-benzoic Acid

HRID 1825809Notes

Reaction equation

HRID 1825809 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].F[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[S:19]([OH:21])=[O:20].[OH-].[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[S:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 805982-BromobenzenethiolHCID 106796785-Carboxy-2-fluorobenzenesulfinic acid

Product 1

HCID 221394104-(2-Bromo-phenylsulfanyl)-3-sulfino-benzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

2-Bromobenzenethiol (25 g, 132 mmol) was added to a solution of 4-fluoro-3-sulfino-benzoic acid (13.5 g, 66 mmol) and NaOH pellets (11 g, 264 mmol) in water (30 ml). The yellow mixture was then degassed for 10 minutes and then heated to 140° C. for 48 hours. The reaction was then cooled to 0° C. and acidified to pH 4–5 (pH paper) with concentrated HCl. The precipitate formed was filtered, washed with hexane and was dried in a vacuum dessicator over activated silica overnight (20.69 g, 84%). m/z (LC-MS, ESP), RT=3.67 min, (M−−1)=373.

Workup

  1. customThe yellow mixture was then degassed for 10 minutes
  2. temperatureThe reaction was then cooled to 0° C.
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. washwashed with hexane
  6. customwas dried in a vacuum dessicator over activated silica overnight (20.69 g, 84%)

Sources & evidence

ORD record
ord-270abed976bf46dbb74feeddd5a3d306
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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