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

HRID 731975Notes

Reaction equation

HRID 731975 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.C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>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:22])=[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 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 22.3 grams (0.062 mole) of 4-[4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenoxy]butan-1-ol and 20.6 grams (0.062 mole) of carbon tetrabromide in 250 mL of methylene chloride was cooled to 10° C. and 17.9 grams (0.068 mole) of triphenylphosphine was added in one portion. Upon completion of addition the reaction mixture was warmed 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 25% methylene chloride in hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 21.3 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 25% methylene chloride in hexane as an eluant
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae1a1e944eab421083986220e0a641b0
Source dataset
uspto-grants-2009_09
Patent number
US07585891B2

Reaction notes

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