4-Bromophenol → HCID 19382485, compound

HRID 2400203Notes

Reaction equation

HRID 2400203 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:7]=1.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1>CN(C=O)C>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([CH:12]([O:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)[CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:10][CH:11]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 78084-BromophenolHCID 19382487HCID 19382487, compound

Product 1

HCID 19382485HCID 19382485, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the crude product (5.5 g) of Step 2, 4-bromophenol (5.2 g) and 2 drops of Triton B in 30 mL of DMF was heated for 8 hrs. in a 160° C. oil bath. The mixture was then cooled to r.t., quenched with 100 mL of 2N NaOH, and extracted with 200 mL of Et2O. The extract was dried over NaSO4 and concentrated. The crude product was purified by flash chromatography eluted with 2.5:1 Hexane/EtOAc to give 5.2 g of the title compound.

Workup

  1. temperaturewas heated for 8 hrs
  2. customin a 160° C.
  3. customquenched with 100 mL of 2N NaOH
  4. extractionextracted with 200 mL of Et2O
  5. dry with materialThe extract was dried over NaSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washeluted with 2.5:1 Hexane/EtOAc

Sources & evidence

ORD record
ord-b9e21fc5b4454b3bbb6d3df26da71b99
Source dataset
uspto-grants-1995_09
Patent number
US05453443

Reaction notes

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