Carbon tetrabromide → HCID 22913643, compound

HRID 2039368Notes

Reaction equation

HRID 2039368 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12]O)=[C:6]([F:14])[C:5]=1[F:15])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][Br:36])=[C:6]([F:14])[C:5]=1[F:15])[CH3:2]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 68153618HCID 68153618, compound

Product 1

HCID 22913643HCID 22913643, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(4-Ethoxy-2,3-difluorophenyl)propanol (s21) (9.4 g) and triphenylphosphine (17.1 g) were dissolved in methylene chloride (100 ml). Carbon tetrabromide (17.3 g) in methylene chloride (100 ml) solution was slowly added dropwise to the solution at room temperature, and the mixture was stirred at room temperature for another 3 hours. The reaction mixture was treated with a saturated aqueous solution of sodium hydrogencarbonate, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to leave a residue, pale yellow solids. The residue was purified by column chromatography with heptane as an eluent and silica gel as a stationary phase powder to give 3-(4-ethoxy-2,3-difluorophenyl) bromopropane (s22) (11.5 g). The yield based on the compound (s21) was 94.8%.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layers were washed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe solution was concentrated under reduced pressure
  5. customto leave a residue, pale yellow solids
  6. customThe residue was purified by column chromatography with heptane as an eluent

Sources & evidence

ORD record
ord-51b01ec17c0b4dc783bf29ed20ed2e5f
Source dataset
uspto-grants-2013_11
Patent number
US08580146B2

Reaction notes

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