Water → 5-Bromo-2-methyl-2,3-dihydro-1-benzofuran

HRID 638361Notes

Reaction equation

HRID 638361 reaction equation
[Br:1]Br.[CH3:3][CH:4]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5]1.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:11]1[CH:10]=[CH:9][C:7]2[O:8][CH:4]([CH3:3])[CH2:5][C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 1011302,3-Dihydro-2-methylbenzofuranHCID 516892Sodium Bicarbonate

Product 1

HCID 133016015-Bromo-2-methyl-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 215 ml of bromine in 450 ml of methylene chloride is added dropwise over 21/2 hours to an ice-cooled mixture of 562.3 g of 2,3-dihydro-2-methylbenzo[b]furan, 1600 ml of methylene chloride, 1600 ml of water and 352.5 g of sodium bicarbonate. After the mixture has been stirred for another 11/2 hours at the same temperature, the aqueous phase is separated and extracted with two 300 ml portions of methylene chloride. The combined organic phases are washed with 2×250 ml of water, dried over sodium sulfate and concentrated. After removal of all constituents having a boiling point below 99° C. under a pressure of 8 mbar, there are obtained 750.7 g of 5-bromo-2,3-dihydro-2-methylbenzo[b]furan as residue.

Workup

  1. temperaturecooled
  2. customthe aqueous phase is separated
  3. extractionextracted with two 300 ml portions of methylene chloride
  4. washThe combined organic phases are washed with 2×250 ml of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customAfter removal of all constituents

Sources & evidence

ORD record
ord-b1b43d5a3213448383d19baeadbfb6d7
Source dataset
uspto-grants-1985_12
Patent number
US04560771

Reaction notes

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