Carbon tetrabromide → HCID 86719449, compound

HRID 1481636Notes

Reaction equation

HRID 1481636 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[CH2:6]([Si:9]([CH2:24][CH:25]=[CH2:26])([CH2:21][CH:22]=[CH2:23])[CH2:10][CH2:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16](CO)=[CH:15][CH:14]=1)[CH:7]=[CH2:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:24]([Si:9]([CH2:6][CH:7]=[CH2:8])([CH2:21][CH:22]=[CH2:23])[CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:1][Br:5])=[CH:19][CH:20]=1)[CH:25]=[CH2:26]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86719448HCID 86719448, compound

Product 1

HCID 86719449HCID 86719449, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 ml of methylene chloride and CBr4 (4.97 g, 15.0 mmol) were slowly added to 4-{3-(triallylsilyl)propyl}benzyl alcohol (5) (3.0 g, 10.0 mmol) and triphenylphosphine (PPh3) (3.93 g, 15.0 mmol) under a nitrogen atmosphere, and the mixture was stirred for 1 hour. Cooled distilled water was added to the reaction mixture. The aqueous layer was extracted with methylene chloride, and the combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under a reduced pressure to give a crude product. The crude product was purified by separating by silica gel column chromatography (elution solvent: n-hexane/ethyl acetate=20/1) to give 4-{3-(triallylsilyl)propyl}benzyl bromide (6) (yield amount: 2.80 g, yield: 77%), as shown in the following chemical reaction formula.

Workup

  1. temperatureCooled
  2. distillationdistilled water
  3. additionwas added to the reaction mixture
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under a reduced pressure
  8. customto give a crude product
  9. customThe crude product was purified
  10. customby separating by silica gel column chromatography (elution solvent: n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-24310ff5a93947f1bbacfc1545cca106
Source dataset
uspto-grants-2016_08
Patent number
US09409929B2

Reaction notes

Loading…