4-Bromophenol → HCID 69144624, compound

HRID 404919Notes

Reaction equation

HRID 404919 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][N:3]=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.[H-].[Na+].C1OCCOCCOCCOCCOCCOC1.[OH-].[Na+]>CS(C)=O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:4][N:3]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 78084-BromophenolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 69169795HCID 69169795, compound

Product 1

HCID 69144624HCID 69144624, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of Example 69A (˜53.05 mmol) and 4-bromophenol (13.80 g, 79.76 mmol) in DMSO (50 mL) cooled with an ice-bath was added NaH (60%, 3.20 g, 80.0 mmol) in several portions. After the addition, the mixture was stirred at room temperature for 10 minutes. To this was added 18-crown-6 (16.0 mL, 80.6 mmol). The reaction mixture was heated to 160° C. for 60 hours. The mixture was poured into 1N NaOH, extracted with ethyl acetate (2×). The combined extracts were washed with water (1×), brine (1×), dried over MgSO4 and concentrated. The residue was purified on silica gel eluting with ethyl acetate and hexane to give the desired product as yellow oil (11.1 g).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was heated to 160° C. for 60 hours
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined extracts were washed with water (1×), brine (1×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel eluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-25297282d8e64bb1a2fd55f9555611f4
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

Loading…