Benzyl Bromide → 4-Benzyloxy-2-(trifluoromethyl)benzayl alcohol

HRID 1946308Notes

Reaction equation

HRID 1946308 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:10]([F:13])([F:12])[F:11].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>C(O)C.ClCCl>[C:15]1([CH2:14][O:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[C:4]([C:10]([F:11])([F:12])[F:13])[CH:5]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 595479534-(Hydroxymethyl)-3-(trifluoromethyl)phenol

Product 1

HCID 595479924-Benzyloxy-2-(trifluoromethyl)benzayl alcohol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(hydroxymethyl)-3-(trifluoromethyl)phenol (for a preparation see Intermediate 17)(3.86 g, 20.1 mmol) in ethanol (80 mL) was added benzyl bromide (2.4 ml, 20.2 mmol, Aldrich) and then 2 M sodium hydroxide (11 ml, 22 mmol). The mixture was stirred at ambient temperature overnight under nitrogen. The solvent was removed in vacuo to leave an aqueous suspension. The residue was partitioned between dichloromethane (100 ml) and water (100 ml). The phases were separated and the aqueous phase extracted with dichloromethane (50 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to leave an oil. The residue was loaded in dichloromethane and purified on silica 100 g using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (4.68 g);

Workup

  1. customThe solvent was removed in vacuo
  2. customto leave an aqueous suspension
  3. customThe residue was partitioned between dichloromethane (100 ml) and water (100 ml)
  4. customThe phases were separated
  5. extractionthe aqueous phase extracted with dichloromethane (50 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customto leave an oil
  10. custompurified on silica 100 g
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-e9aae98beb2a4e40939efa40b3a4fcee
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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