Isobutylene → 1-Bromo-3-tert-butoxybenzene

HRID 1636179Notes

Reaction equation

HRID 1636179 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].C(=O)=O.CC(C)=O.[Br:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.FC(F)(F)S(O)(=O)=O.C(N(CC)CC)C>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([O:19][C:2]([CH3:3])([CH3:1])[CH3:4])[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 8255IsobutyleneHCID 8471TriethylamineHCID 115633-BromophenolHCID 62406Trifluoromethanesulfonic acidHCID 18522661Acetone cardice

Product 1

HCID 135462901-Bromo-3-tert-butoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-75 °C

Procedure

Condensed isobutylene (100 ml) was added via a dry ice/acetone cold finger, to dichloromethane (70 ml) at −30° C., followed by a solution of 3-bromophenol (21.5 g, 125 mmol) in dichloromethane (30 ml). Trifluoromethanesulphonic acid (1.5 g, 10.0 mmol) was added dropwise, the reaction cooled to −75° C., and stirred for 2 hours. Triethylamine (1.4 ml, 10.0 mmol) was then added, the solution allowed to warm to room temperature and then concentrated in vacuo to remove the isobutylene. The remaining solution was washed with water, dried (Na2SO4), filtered and evaporated to give the desired product as a pale yellow oil, (33 g, slightly impure).

Workup

  1. temperatureto warm to room temperature
  2. concentrationconcentrated in vacuo
  3. customto remove the isobutylene
  4. washThe remaining solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e196ecd2b7e4466a918e08342b1e5f7f
Source dataset
uspto-grants-2003_01
Patent number
US06511993B1

Reaction notes

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