Bromine → 4-(3-Bromo-2-methoxy-5-methylphenyl)-butyric acid

HRID 2290929Notes

Reaction equation

HRID 2290929 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].CC([O-])=O.[Na+].[Br:21]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:21][C:8]1[C:3]([O:2][CH3:1])=[C:4]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 24408BromineHCID 2824524-(2-Methoxy-5-methylphenyl)butanoic acidHCID 517045Sodium AcetateHCID 23665763Sodium Bisulfite

Product 1

HCID 202306874-(3-Bromo-2-methoxy-5-methylphenyl)-butyric acidYield 104.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 4-(2-methoxy-5-methylphenyl)-butyric acid (74 g, 0.36 mole), NaOAc (29.8 g, anhydrous), and glacial acetic acid (710 mL) was stirred under N2 at room temperature. as a solution of bromine (22 mL, 0.43 mole) and glacial acetic acid (185 mL) was added dropwise. The reaction mixture was stirred at room temperature for 20 hours. 10% aqueous sodium bisulfite (400 mL) was added and the solution was extracted with CH2Cl2. The combined extracts were washed with water, 10% aqueous sodium thiosulfate, water, saturated aqueous. NaCl, dried (MgSO4), filtered, and evaporated to yield 108 g brown solid which was recrystallized from hexane to yield 76 g white solid, (74%); m+ 286.

Workup

  1. extractionthe solution was extracted with CH2Cl2
  2. washThe combined extracts were washed with water, 10% aqueous sodium thiosulfate, water
  3. dry with materialNaCl, dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-28e6ff3030214221915f54e4e071a111
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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