Carbon tetrabromide → HCID 54216132, compound

HRID 2242521Notes

Reaction equation

HRID 2242521 reaction equation
[Cl:1][C:2]([Cl:18])=[CH:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]([Cl:16])[C:9]([O:10][CH2:11][CH2:12]O)=[C:8]([Cl:17])[CH:7]=1.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]([Cl:18])=[CH:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]([Cl:16])[C:9]([O:10][CH2:11][CH2:12][Br:20])=[C:8]([Cl:17])[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22006767HCID 22006767, compound

Product 1

HCID 54216132HCID 54216132, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2.5 grams (0.0075 mole) of 2-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]ethan-1-ol and 3.1 grams (0.0094 mole) of carbon tetrabromide in 150 mL of methylene chloride was cooled to 0-4° C. and 6.0 grams (0.0152 mole) of triphenylphosphine was added portion-wise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred during an 18 hour period. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 1:5 ethyl acetate:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 2.7 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  3. customThe residue was purified with column chromatography on silica gel using 1:5 ethyl acetate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ee269448fe6465ab41513fe038d4628
Source dataset
uspto-grants-2010_03
Patent number
US07671201B2

Reaction notes

Loading…