Bromine → 7-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde

HRID 15173

Reaction equation

HRID 15173 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].[Br:17]Br>C(O)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:17][C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 7359012,3-Dihydrobenzofuran-5-carboxaldehyde

Product 1

HCID 185261827-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehydeYield 91.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of 2,3-dihydro-1-benzofuran-5-carbaldehyde (1.0 g, 6.75 mmol) in glacial acetic acid (8 ml) was added sodium acetate (664 mg, 8.1 mmol) and bromine (0.7 ml, 13.5 mmol) at 10° C. slowly. The reaction was stirred for 2 h at room temperature. The reaction was diluted with a saturated aqueous solution of sodium thiosulfate (10 ml), washed with a saturated aqueous solution of sodium bicarbonate, and then extracted with ethyl acetate. Organics were combined, dried over sodium sulfate and dried in vacuo to give the desired compound (1.4 g, 91%).

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ccbd064e0acc467fae69302d4fe79d5f
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Linked notes

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