Phosphorus tribromide → HCID 66891549, compound

HRID 253264Notes

Reaction equation

HRID 253264 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[C:5]([F:12])=[CH:4][C:3]=1[CH2:13]OC1CCCCO1.P(Br)(Br)[Br:22]>C1(C)C=CC=CC=1>[Br:22][CH2:13][C:3]1[CH:4]=[C:5]([F:12])[C:6]2[O:7][CH2:8][CH2:9][O:10][C:11]=2[C:2]=1[F:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 66890454HCID 66890454, compound

Product 1

HCID 66891549HCID 66891549, compoundYield 160%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5,8-difluoro-6-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2,3-dihydro-1,4-benzodioxine (785 mg, 2.74 mmol) in toluene (5 mL) was added phosphorous tribromide (155 μl, 1.65 mmol) and the solution was stirred at room temperature for 15 hrs. The solution was concentrated in-vacuo, and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic portion was washed with brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford 700 mg, 2.64 mmol (96%) of 6-(bromomethyl)-5,8-difluoro-2,3-dihydro-1,4-benzodioxine as a pale yellow oil. 1H NMR (400 MHz, CDCl3): 6.68 (q, 1H), 4.33 (s, 2H), 4.35 (s, 4H); GC/MS (EI) for C9H7O2F2Br: 265 (M+).

Workup

  1. concentrationThe solution was concentrated in-vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic portion was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-ceb3851b87f048f4a3031145ef8e7ff5
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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