N-bromobutanimide → 2-(4-Bromomethyl-3-trifluoromethyl-phenyl)-propan-2-ol

HRID 1970190Notes

Reaction equation

HRID 1970190 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:12]([F:13])([F:14])[F:15]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67241275HCID 67241275, compound

Product 1

HCID 672413992-(4-Bromomethyl-3-trifluoromethyl-phenyl)-propan-2-olYield 76%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-(4-Methyl-3-trifluoromethyl-phenyl)-propan-2-ol (0.436 g, 2 mmol), N-Bromosuccinimide (356 mg, 2 mmol) and benzoyl peroxide (15 mg) in CCl4 (8 mL) was stirred at 85° C. for 16 hrs. The reaction mixture was then partitioned between saturated aqueous NaHCO3 and DCM. DCM layer was dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid which was purified via flash chromatography (15% EtOAc in n-heptane) to yield the title compound as a solid (450 mg, 76%)

Workup

  1. customThe reaction mixture was then partitioned between saturated aqueous NaHCO3 and DCM
  2. dry with materialDCM layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customto yield a crude solid which
  6. customwas purified via flash chromatography (15% EtOAc in n-heptane)

Sources & evidence

ORD record
ord-e8ee87f661c146acb822e605fae1ca3e
Source dataset
uspto-grants-2013_04
Patent number
US08426604B2

Reaction notes

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