2-Bromophenol → 1-Bromo-2-(3-fluorophenoxy)benzene

HRID 1254256Notes

Reaction equation

HRID 1254256 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].CCN(CC)CC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[Br:11]

Participants

6

Reactant 3

HCID 72442-BromophenolHCID 8471TriethylamineHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 184235101-Bromo-2-(3-fluorophenoxy)benzeneYield 48%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-fluorophenylboronic acid (2.10 g, 15 mmol), 2-bromophenol (1.77 g, 10 mmol) and Cu(OAc)2 (0.93 g, 5 mmol) in anhydrous CH2Cl2 (25 mL) was added activated 4 Å molecular sieves (˜0.1 g), followed by anhydrous Et3N (3.5 mL, 25 mmol). The resulting dark green solution was stirred at rt for 48 h. The mixture was evaporated under reduced pressure and the residue was washed several times with Et2O (˜150 mL). The Et2O solution was washed with sat'd aq NH4Cl, and 1 N aq HCl. The organic layer was evaporated and the crude product was purified by flash column chromatography to give 1-(3-fluorophenoxy)-2-bromobenzene (1.28 g, 48%) as clear oil.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. washthe residue was washed several times with Et2O (˜150 mL)
  3. washThe Et2O solution was washed with sat'd aq NH4Cl, and 1 N aq HCl
  4. customThe organic layer was evaporated
  5. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-71cb06efe396404498c0446bbe565386
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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