Phosphorus tribromide → HCID 18415115, compound

HRID 991979Notes

Reaction equation

HRID 991979 reaction equation
P(Br)(Br)[Br:2].[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([Br:25])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:22]([CH3:24])[CH3:23])[CH:16]=1)[CH2:9]O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([Br:25])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:22]([CH3:24])[CH3:23])[CH:16]=1)[CH2:9][Br:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 18415111HCID 18415111, compound

Product 1

HCID 18415115HCID 18415115, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of PBr3 (125 mg, 0.463 mmol) in 5 ml of CH2Cl2 was added dropwise, under nitrogen, to a stirred solution of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)-benzylalcohol (Example 12) (385 mg, 0.925 mmol) in 20 ml CH2Cl2 at 0° C. The reaction mixture was left to stand at room temperature over night and then diluted with CH2Cl2. The organic phase was washed with water, dried over MgSO4 and concentrated. The residue was purified by column chromathography (silica gel, 75:25 petroleum-ether/EtOAc) to give 160 mg (36%) of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)benzylbromide.

Workup

  1. waitThe reaction mixture was left
  2. waitto stand at room temperature over night
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromathography (silica gel, 75:25 petroleum-ether/EtOAc)

Sources & evidence

ORD record
ord-8fce45654d48434bbd1abd8dd5127c54
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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