Bromine → HCID 59578637, compound

HRID 1774568Notes

Reaction equation

HRID 1774568 reaction equation
[Cl:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH3:12])=[CH:4][CH:3]=1.[Br:13]Br>CC(O)=O.C1(C)C=CC=CC=1>[Br:13][C:4]1[CH:3]=[C:2]([Cl:1])[C:11]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]=1[CH3:12]

Participants

5

Reactant 2

HCID 24408BromineHCID 59578574HCID 59578574, compound

Product 1

HCID 59578637HCID 59578637, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 1140TolueneSolvent

Procedure

A mixture of the 8-chloro-5-methyl-3,4-dihydro-2H-1-benzopyran (7d) (5.74 g, 31.4 mmol) and acetic acid (75 mL) is treated with bromine (1.93 mL, 37.7 mmol) in AcOH (35 mL). The mixture was stirred at room temperature for 15 minutes, then diluted with toluene (100 mL). The mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (70 mL) and successively washed with a 15% sodium thiosulfate solution (50 mL) and a saturated solution of sodium hydrogenocarbonate (50 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The product was recrystallized in ethanol, to provide 6-bromo-8-chloro-5-methyl-3,4-dihydro-2H-1-benzopyran (7e) (4.44 g, 17.0 mmol, 54%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (70 mL)
  3. washsuccessively washed with a 15% sodium thiosulfate solution (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was recrystallized in ethanol

Sources & evidence

ORD record
ord-81a7780b93334598967fa7619c1e3335
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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