Hydrochloric Acid → 2-Bromo-α,α-dimethylbenzenepropanoic acid

HRID 2172720Notes

Reaction equation

HRID 2172720 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12]CC)=[O:11].[OH-].[Na+].Cl>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH3:16])([CH3:15])[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68379166HCID 68379166, compound

Product 1

HCID 100380662-Bromo-α,α-dimethylbenzenepropanoic acidYield 47%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the crude ester (482 mg) in dioxane (2 mL) was combined with aqueous sodium hydroxide (20%, 4 mL) and stirred at room temperature for 2 hrs. The reaction mixture was diluted with ethyl acetate and the aqueous fraction was acidified to pH 2 with conc. hydrochloric acid. After extraction with ethyl acetate, the combined organic fractions were dried over sodium sulfate and concentrated under vacuum to give 121 mg (47% yield for two steps) of 3-(2-bromophenyl)-2,2-dimethylpropanoic acid as a white solid. The crude carboxylic acid was used in the next step without further purification: MS m/z: 255.0 (M−1).

Workup

  1. extractionAfter extraction with ethyl acetate
  2. dry with materialthe combined organic fractions were dried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e022ffa52da747c6af2d88271b3f0acd
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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