Boron tribromide → HCID 22285674, compound

HRID 2108613Notes

Reaction equation

HRID 2108613 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:21])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH:18]([CH3:20])[CH3:19])[CH:12]=1)[CH2:5]O.B(Br)(Br)[Br:23]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:21])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH:18]([CH3:20])[CH3:19])[CH:12]=1)[CH2:5][Br:23]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9818775HCID 9818775, compound

Product 1

HCID 22285674HCID 22285674, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dichloro-4-(4′-hydroxy-3′-iso-propyl-phenoxy)benzyl alcohol in CH2Cl2 (5.0 mL) at −78° C. is added BBr3. The reaction mixture is stirred at room temperature for 16 h, poured into ice water and extracted with ethyl acetate. The organic layer is dried over MgSO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography on silica gel, eluting with acetone-hexanes to afford 3,5-dichloro-4-(4′-hydroxy-3′-iso-propyl-phenoxy)benzyl bromide.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by column chromatography on silica gel
  6. washeluting with acetone-hexanes

Sources & evidence

ORD record
ord-ee0f81aafc43440187807e3def7a189f
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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