Cesium carbonate → HCID 86697121, compound

HRID 471455Notes

Reaction equation

HRID 471455 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[CH3:11][C:12]1([O:15][CH2:14]1)[CH3:13].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:11][C:12]([CH3:14])([OH:15])[CH3:13])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11208Isobutylene oxideHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 86697121HCID 86697121, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-3,5-dimethylphenol (4.0 g), isobutylene oxide (2.0 g) and Cs2CO3 (9.7 g) in N,N-dimethylformamide (10 mL) are stirred at 100° C. for 20 h. After cooling the mixture is partitioned between water and EtOAc, the organic layer dried (MgSO4) and concentrated. Purification of the residue by column chromatography (silica gel, n-hexane:EtOAc 100:0 to 50:50 gradient) gives the desired compound (5.6 g, content ca. 97%).

Workup

  1. temperatureAfter cooling the mixture
  2. customis partitioned between water and EtOAc
  3. dry with materialthe organic layer dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the residue by column chromatography (silica gel, n-hexane:EtOAc 100:0 to 50:50 gradient)

Sources & evidence

ORD record
ord-260d953fdb4b4fe4ad3ec6d282ec815c
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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