4-Bromophenol → HCID 89442955, compound

HRID 1474630Notes

Reaction equation

HRID 1474630 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1(Br)[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].CCN(C(C)C)C(C)C>C(#N)C.C(OC(=O)C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 81531DiisopropylethylamineHCID 86183552HCID 86183552, compound

Product 1

HCID 89442955HCID 89442955, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromophenol (500 mg, 2.9 mmol) in ACN (14.5 mL), 2,2-dibromo cyclopentanone (1.4 g, 8.7 mmol) and DIPEA (500 mg, 2.9 mmol) were added. The resulting mixture was stirred at r.t overnight. After completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethylacetate (150 mL), washed with water (50 mL) and brine (50 mL) successively. The combined organic layers were dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 1:9 EtOAc:hexane) to provide title compound (461 mg, 63%) as pale brown liquid.

Workup

  1. customAfter completion of the reaction
  2. washwashed with water (50 mL) and brine (50 mL) successively
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe volatiles were evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 1:9 EtOAc:hexane)

Sources & evidence

ORD record
ord-c0164ab699594083aa1689e16530de22
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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