Carbon tetrabromide → 1-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-4-bromobutane

HRID 1611458Notes

Reaction equation

HRID 1611458 reaction equation
[Cl:1][C:2]([Cl:20])=[CH:3][CH2:4][O:5][C:6]1[CH:17]=[C:16]([Cl:18])[C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14]O)=[C:8]([Cl:19])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:41]>C(Cl)Cl>[Cl:1][C:2]([Cl:20])=[CH:3][CH2:4][O:5][C:6]1[CH:17]=[C:16]([Cl:18])[C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:41])=[C:8]([Cl:19])[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 222571304-{2,6-Dichloro-4-[(3,3-dichloroprop-2-EN-1-YL)oxy]phenoxy}butan-1-OL

Product 1

HCID 222571451-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-4-bromobutaneYield 144.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 7.3 grams (0.020 mole) of 4-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]butan-1-ol in 400 mL of methylene chloride was cooled in an ice bath and, in turn, 5.5 grams (0.021 mole) of triphenylphosphine and 6.9 grams (0.021 mole) of carbon tetrabromide were added. Upon completion of addition the reaction mixture was stirred with continued cooling for one hour, then it 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 hexane and a mixture of 1:1 methylene chloride and heptane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 12.2 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwere added
  2. additionUpon completion of addition the reaction mixture
  3. temperaturewith continued cooling for one hour
  4. stirringstirred during an 18-hour period
  5. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  6. customThe residue was purified with column chromatography on silica gel
  7. additiona mixture of 1:1 methylene chloride and heptane as an eluant
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9296b5af41c94e6db45ac110c65e2989
Source dataset
uspto-grants-2006_01
Patent number
US06987194B2

Reaction notes

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