3-Phenoxyphenol → HCID 15744514, compound

HRID 1820691Notes

Reaction equation

HRID 1820691 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15]N1C(=O)CCC1=O>CC#N.C(O)(C(F)(F)F)=O>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([OH:14])=[CH:9][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 128423-PhenoxyphenolHCID 31398Chlorosuccinimide

Product 1

HCID 15744514HCID 15744514, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-Phenoxyphenol (1.00 g, 5.4 mmol) was dissolved in MeCN (40 mL) and TFA (0.5 mL). N-Chlorosuccinimide (717 mg, 5.4 mmol) was added and the reaction stirred at ambient temperature for 48 h. Solvents were removed in vacuo to afford the crude product as an oil (2.15 g). 300 mg of this crude material was purified by HPLC to afford in order of elution 4-chloro-3-phenoxyphenol (68 mg, 0.31 mmol, 41%) M.S. (ESI) (m/z): 219,221 [M−H]−; and 6-chloro-3-phenoxyphenol (73 mg, 0.33 mmol, 44%) M.S. (ESI) (m/z): 219,221 [M−H]−.

Workup

  1. customSolvents were removed in vacuo
  2. customto afford the crude product as an oil (2.15 g)
  3. custom300 mg of this crude material was purified by HPLC

Sources & evidence

ORD record
ord-0d54f565711d4410a2c6117e390c6074
Source dataset
uspto-grants-2009_10
Patent number
US07605170B2

Reaction notes

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