3-Phenoxyphenol → HCID 57891891, compound

HRID 1820690Notes

Reaction equation

HRID 1820690 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.[Br:15]Br>C(Cl)Cl>[Br: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

4

Reactant 2

HCID 128423-PhenoxyphenolHCID 24408Bromine

Product 1

HCID 57891891HCID 57891891, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Phenoxyphenol (700 mg, 3.8 mmol) was stirred at 0° C. in DCM (7 mL) and bromine (0.154 mL, 3.0 mmol) was added dropwise. The reaction was stirred at ambient temperature for 10 min and then the solvents removed in vacuo to afford a crude oil which was purified by preparative HPLC to afford, in order of elution, 4-bromo-3-phenoxyphenol (126 mg, 0.5 mmol, 16%) M.S. (ESI) (m/z): 263,265 [M−H]−; and 4,6-dibromo-3-phenoxyphenol (201 mg, 0.6 mmol, 39%) M.S. (ESI) (m/z): 341, 343, 345 [M−H]−

Workup

  1. customthe solvents removed in vacuo
  2. customto afford a crude oil which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-c561b882bf55444289b0f6187a88e590
Source dataset
uspto-grants-2009_10
Patent number
US07605170B2

Reaction notes

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