Isobutylene oxide → HCID 86697121, compound

HRID 2170926Notes

Reaction equation

HRID 2170926 reaction equation
[CH3:1][C:2]1([CH3:5])[CH2:4][O:3]1.[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[CH:9][C:8]=1[CH3:15]>CN(C=O)C>[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([O:14][CH2:1][C:2]([CH3:5])([OH:3])[CH3:4])=[CH:9][C:8]=1[CH3:15]

Participants

4

Reactant 2

HCID 11208Isobutylene oxideHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 86697121HCID 86697121, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a microwave vial 2.20 g (0.03 mmol) of 2,2-dimethyloxirane are added to a suspension of 6.00 g (0.03 mmol) of 4-bromo-3,5-dimethylphenol and 11.0 g (0.08 mmol) K2OC3 in 6.0 ml DMF. The vial is sealed and the mixture is heated for 48 hours to 120° C. After cooling to r.t., the mixture is partitioned between sat. aq. Na2CO3 solution and EtOAc. The aq. phase is extracted twice with EtOAc and the combined organic phases are dried and concentrated. The residue is chromatographed on silica gel (CH/EtOAc 100:050:50) to give the title compound. Yield: 2.9 g; LC (method 4): tR=1.76 min; Mass spectrum (ESI+): m/z=273 [M+H]+.

Workup

  1. customThe vial is sealed
  2. temperaturethe mixture is heated for 48 hours to 120° C
  3. customthe mixture is partitioned between sat. aq. Na2CO3 solution and EtOAc
  4. extractionThe aq. phase is extracted twice with EtOAc
  5. customthe combined organic phases are dried
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (CH/EtOAc 100:050:50)

Sources & evidence

ORD record
ord-42d6ea75adde4a4587b09e4bb443807f
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

Loading…