Benzyl Alcohol → 1-(Benzyloxy)-3-bromo-5-fluorobenzene

HRID 1990737Notes

Reaction equation

HRID 1990737 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[CH:17]=[C:16](F)[CH:15]=[C:14]([F:19])[CH:13]=1.O>C1COCC1>[Br:11][C:12]1[CH:17]=[C:16]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:15]=[C:14]([F:19])[CH:13]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 1363131-Bromo-3,5-difluorobenzene

Product 1

HCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzeneYield 98,445.398%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% dispersion in oil, 24.0 g, 0.48 mol) was added portionwise to a stirred solution of anhydrous benzyl alcohol (64.5 g, 0.60 mol) in THF (1.0 L). After the mixture was stirred for 1 h, a solution of 1-bromo-3,5-difluorobenzene (76.8 g, 0.40 mmol) in THF (100 mL) was added dropwise over a period of 1 h. The reaction was stirred at room temperature for 2 d. Water (400 mL) was added and the THF was removed in vacuo. The aqueous layer was extracted with hexane (3× 150 mL). The combined organic extracts were washed with 2N NaOH (2× 100 mL) then, dried (Na2SO4), filtered and concentrated in vacuo to afford the sub-title compound (110.7 g, 98%) as a light yellow oil that was used without further purification.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 d
  2. customthe THF was removed in vacuo
  3. extractionThe aqueous layer was extracted with hexane (3× 150 mL)
  4. washThe combined organic extracts were washed with 2N NaOH (2× 100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d63442edd78e484eb2e330f829672c6d
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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