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

HRID 1271831Notes

Reaction equation

HRID 1271831 reaction equation
[Cl:1][C:2]([Cl:19])=[CH:3][CH2:4][O:5][C:6]1[CH:16]=[C:15]([Cl:17])[C:9]([O:10][CH2:11][CH2:12][CH2:13]O)=[C:8]([Cl:18])[CH:7]=1.C(Br)(Br)(Br)[Br:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]([Cl:19])=[CH:3][CH2:4][O:5][C:6]1[CH:16]=[C:15]([Cl:17])[C:9]([O:10][CH2:11][CH2:12][CH2:13][Br:21])=[C:8]([Cl:18])[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 113139803-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-ol

Product 1

HCID 108840691-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropaneYield 188.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3.5 grams (0.010 mole) of 3-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]propan-1-ol and 3.3 grams (0.010 mole) of carbon tetrabromide in 50 mL of methylene chloride was cooled to 0–4° C. and 2.9 grams (0.011 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 a 42 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 1:3 methylene chloride:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 7.7 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 1:3 methylene chloride
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-212c3d2414b24700ab62ae566bce5a34
Source dataset
uspto-grants-2007_04
Patent number
US07208450B2

Reaction notes

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