Benzoyl Peroxide → HCID 21035356, compound

HRID 1867154Notes

Reaction equation

HRID 1867154 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C1C(=O)N([Br:23])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][O:7][C:6]1[CH:14]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[CH2:15][Br:23])[CH3:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 22050564HCID 22050564, compound

Product 1

HCID 21035356HCID 21035356, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of ethyl (5-fluoro-2-methylphenoxy)acetate (from Step 1) (0.65 g, 3.06 mmol), NBS (0.65 g, 3.68 mmol), and benzoyl peroxide (0.05 g, 0.21 mmol) in CCl4 (7.0 mL) were refluxed at 90° C. for 2.5 h. Additional NBS (0.16 g, 0.92 mmol) added, and reaction continued overnight. Solid filtered and filtrate concentrated onto silica gel. Purified by flash column chromatography using hexane and 2.5% EtOAc/hexane as eluent. Product obtained as yellow liquid (0.27 g, 30%). 1H NMR (CD3OD/400 MHz) δ7.37 (m, 1H), 6.69 (m, 2H), 4.80 (s, 2H), 4.60 (s, 2H), 4.23 (q, 2H, J=7.2 Hz), 1.27 (t, 3H, J=7.2 Hz).

Workup

  1. customreaction continued overnight
  2. filtrationSolid filtered
  3. concentrationfiltrate concentrated onto silica gel
  4. customPurified by flash column chromatography

Sources & evidence

ORD record
ord-89736cc043684ec7ac9f168c4466088c
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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