Phosphorus tribromide → HCID 18415110, compound

HRID 991982Notes

Reaction equation

HRID 991982 reaction equation
P(Br)(Br)[Br:2].[CH3:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH3:25])[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>[CH3:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH3:25])[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 18415113HCID 18415113, compound

Product 1

HCID 18415110HCID 18415110, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of PBr3 (401 mg, 1.48 mmol) in 10 ml of CH2Cl2 was added dropwise, under nitrogen, to a stirred solution of the above alcohol (Example 16, 850 mg) in 20 ml CH2C12 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, 9:1 petroleum-ether/EtOAc) to give 465 mg of 3,5-dimethyl-4-(4-hydroxy-3-isopropyl-phenoxy)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, 9:1 petroleum-ether/EtOAc)

Sources & evidence

ORD record
ord-2f9b623d586049cf8e1ab34ca7bc463a
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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