Bromoacetic Acid → HCID 10633915, compound

HRID 1760244Notes

Reaction equation

HRID 1760244 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[CH:14]([CH3:16])[CH3:15])[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH:17](C1C=CC(C(O)=O)=CC=1)(C)C.C([O-])(O)=O.[Na+].[O-]S([O-])=O.[Na+].[Na+].BrCC(O)=O.[OH-].[Na+]>O>[CH3:17][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[CH:14]([CH3:16])[CH3:15])[C:8]([OH:10])=[O:9])(=[O:4])=[O:3]

Participants

8

Reactant 6

HCID 6227Bromoacetic AcidHCID 108204-Isopropylbenzoic AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 3095103-(Chlorosulfonyl)-4-(propan-2-yl)benzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 10633915HCID 10633915, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

3-Chlorosulfonyl-4-iso-propylbenzoic acid (2.62 g, 10 mmol) [made from 4-iso-propyl benzoic acid in a manner similar to that described in Procedures 7 and 8] was added slowly to a slurry of NaHCO3 (2.52 g, 30 mmol) and Na2SO3 (1.26 g 10 mmol) in water (9 ml) at 75° C. The mixture was stirred for 1 h and then treated with bromoacetic acid (2.08 g, 15 mmol) and NaOH (0.60 g, 15 mmol). The temperature was raised to 105° C. and the mixture heated at reflux for 24 h. The mixture was cooled, acidified to pH 1 and the resultant precipitate collected, washed and dried to give the title compound (1.43 g, 59%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 h
  3. temperatureThe mixture was cooled
  4. customthe resultant precipitate collected
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-0e672e86a19348c48147a765230e95a9
Source dataset
uspto-grants-2005_01
Patent number
US06841560B2

Reaction notes

Loading…