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

HRID 979733

Reaction equation

HRID 979733 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.C(=O)(O)[O-].[Na+].C(Cl)Cl>O>[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 6344DichloromethaneHCID 24408Bromine2×HCID 1011302,3-Dihydro-2-methylbenzofuranHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With efficient stirring, 283 g. (1.77 moles) of bromine are added dropwise at 0°-5° C. to a mixture of 237 g (1.77 moles) of 2,3-dihydro-2-methylbenzo[b]furan, 148.7 g (1.77 moles) of sodium bicarbonate, 500 ml of methylene chloride and 500 ml of water. When the addition of bromine is complete, the mixture is stirred for another 1/2 hour at 20°-25° C. The organic phase is separated, dried over sodium sulfate, concentrated and fractionated in vacuo. Yield: 242 g (66% of theory) of 5-bromo-2,3-dihydro-2-methylbenzo[b]furan and 77 g (15% theory) of 5,7-dibromo-2,3-dihydro-2-methylbenzo[b]furan.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0eefa53de79e45e78ff547734006edb6
Source dataset
uspto-grants-1987_01
Patent number
US04634465

Linked notes

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