Benzyl Alcohol → 1-(Benzyloxy)-3,5-dibromobenzene

HRID 1990741Notes

Reaction equation

HRID 1990741 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]([Br:19])[CH:13]=1>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]([Br:19])[CH:13]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 1370031,3-Dibromo-5-fluorobenzene

Product 1

HCID 147841501-(Benzyloxy)-3,5-dibromobenzeneYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (9.9 g, 0.414 mol, 95% dry) was added in portions to a stirred solution of benzyl alcohol (41.0 g, 0.394 mol) in THF (1.0 L) at room temperature under a nitrogen atmosphere and stirred for 1 h. To this solution was added dropwise 1,3-dibromo-5-fluorobenzene (100.0 g, 0.394 mol). After stirring overnight, the mixture was partitioned with H2O (600 mL) and EtOAc (4× 600 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with hexanes afforded the sub-title compound (101.3 g, 75%) as a yellow oil.

Workup

  1. stirringAfter stirring overnight
  2. customthe mixture was partitioned with H2O (600 mL) and EtOAc (4× 600 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ee5f1cb281c449585123f9dd34296c1
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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