Dichloromethane → 1-Bromo-4-(tert-butoxy)benzene

HRID 1609753Notes

Reaction equation

HRID 1609753 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10](=[CH2:12])[CH3:11].C(Cl)Cl.FC(F)(F)S(O)(=O)=O>C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]([CH3:12])([CH3:11])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 78084-BromophenolHCID 8255IsobutyleneHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 27639591-Bromo-4-(tert-butoxy)benzene

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

4-Bromophenol(57.8 moles, 10.0 g) was added to a -30° C. solution of isobutylene (40 ml) and methylene chloride (50 ml) and then cooled to -78° C. Trifluoromethanesulfonic acid (4 mmoles, 0.35 ml) was added. The mixture was held at -78° C. for 4 hours and then allowed to warm to room temperature. Triethylamine (0.5 ml) was added; the solvent was removed. The residue was chromatographed over silica gel eluted with 1% ethyl acetate in hexane to yield 12.4 g. (MS)

Workup

  1. temperatureto warm to room temperature
  2. customthe solvent was removed
  3. customThe residue was chromatographed over silica gel
  4. washeluted with 1% ethyl acetate in hexane
  5. customto yield 12.4 g

Sources & evidence

ORD record
ord-1580bf44539f4621b4510fb28adaf8cd
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

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