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

HRID 375107Notes

Reaction equation

HRID 375107 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 mmoles, 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-8643db5da15f47ba9948c439a7542f78
Source dataset
uspto-grants-1996_01
Patent number
US05484780

Reaction notes

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