Benzyl Bromide → 2-Benzyloxy-5-trifluoromethyl-benzylalcohol

HRID 392911Notes

Reaction equation

HRID 392911 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:9]=1[CH2:10][OH:11].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:20]([O:7][C:8]1[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:9]=1[CH2:10][OH:11])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 233631292-(Hydroxymethyl)-4-(trifluoromethyl)phenol

Product 1

HCID 179473082-Benzyloxy-5-trifluoromethyl-benzylalcoholYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Cesium carbonate (2.24 g, 6.9 mmol) was added to a solution of 2-hydroxy-5-trifluoromethyl-benzyl alcohol (885 mg, 4.6 mmol) and benzyl bromide (547 μL, 4.6 mmol) in anhydrous DMF (8 mL) at room temperature. The reaction was heated to 50° C. for 2 hours, cooled, diluted with ethyl acetate (25 mL) and washed with water (3×25 mL), brine (1×25 mL), and dried (Na2SO4), filtered and concentrated to afford 1.3 g of the title compound as a colorless solid. 1H NMR (400 MHz. CDCl3) δ 7.6-7.3 (m, 7H); 7.01 (d, 1H, J=9.1 Hz); 5.18 (s, 2H); 4.79 (s, 2H); 2.8 (bs, 1H).

Workup

  1. temperaturecooled
  2. washwashed with water (3×25 mL), brine (1×25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b785364b4ab40d099bc0268f05733f4
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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