Carbon tetrabromide → 4-(1,1-Dimethyl-3,3-dibromo-2-propenyl)anisole

HRID 481523

Reaction equation

HRID 481523 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:13])([CH3:12])[CH:10]=O)=[CH:5][CH:4]=1.[C:14](Br)(Br)([Br:16])[Br:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:12][C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH3:13])[CH:10]=[C:14]([Br:16])[Br:15]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 111376892-(4-Methoxyphenyl)-2-methylpropanal

Product 1

HCID 190664224-(1,1-Dimethyl-3,3-dibromo-2-propenyl)anisoleYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Compound 45 (3.0 g, 17 mmol) and CBr4 (11 g, 34 mmol) in CH2Cl2 (100 ml) was added PPh3 (18 g, 67 mmol) at r.t., and stirred for 1.5 h. The mixture was quenched by the addition of H2O, and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. This was purified by SiO2 chromatography to give Compound 53 (2.5 g, 45%) as a colorless oil.

Workup

  1. customThe mixture was quenched by the addition of H2O
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-7fb77abeec4e4e33acaabbbc6f9447a3
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Linked notes

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