Bromine → 5-Bromo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acid

HRID 445842Notes

Reaction equation

HRID 445842 reaction equation
[Br:1]Br.[CH3:3][C:4]1([CH3:16])[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:6]=2[O:5]1.S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Br:1][C:10]1[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:6]2[O:5][C:4]([CH3:16])([CH3:3])[CH2:8][C:7]=2[CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 27954692,2-Dimethyl-2,3-dihydro-1-benzofuran-7-carboxylic acid

Product 1

HCID 148384015-Bromo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Using a dropping funnel, bromine (0.8 mL, 15.6 mmol) in acetic acid (6 mL) was added to a solution of 2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid (1 g, 5.20 mmol) in acetic acid at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. A 2M solution of sodium sulfite was added until all of the red color disappeared. The volatiles were removed in vacuo and dichloromethane was added and the layers separated. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to yield 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid (667).

Workup

  1. customThe volatiles were removed in vacuo and dichloromethane
  2. additionwas added
  3. customthe layers separated
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fad2d0a3f964ecea481d00fa106802d
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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