Triphenylphosphine dibromide → 3-Tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl bromide

HRID 369822Notes

Reaction equation

HRID 369822 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:8]O)([CH3:4])([CH3:3])[CH3:2].[Br:21]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:8][Br:21])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 539541643-Tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl alcohol

Product 1

HCID 183524953-Tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl bromideYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 500 mL round-bottomed flask equipped with a magnetic stirrer was charged with 3.6 g of 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl alcohol and 25 mL of anhydrous CH2Cl2. The solution was cooled in an ice water bath and was treated with 5.68 g of dibromotriphenylphosphorane (Aldrich). The reaction mixture was warmed to RT, stirred for 2.5 h and then diluted with 100 mL of CH2Cl2. The resulting solution was washed with 5% aqueous NaHCO3 (4×60 mL), dried over anhydrous MgSO4 and concentrated to give a white solid. The crude product was purified by flash chromatography on silica gel (95:5 hexane:EtOAc) to afford 3.86 g (88%) of 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl bromide as a white crystalline solid, m.p. 54-55° C.

Workup

  1. customA 500 mL round-bottomed flask equipped with a magnetic stirrer
  2. temperatureThe solution was cooled in an ice water bath
  3. washThe resulting solution was washed with 5% aqueous NaHCO3 (4×60 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customto give a white solid
  7. customThe crude product was purified by flash chromatography on silica gel (95:5 hexane:EtOAc)

Sources & evidence

ORD record
ord-c3cf79a13c944096b2d414adf166a277
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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