Triphenylphosphine → [2-(Bromomethyl)phenyl](trimethyl)silane

HRID 1768503Notes

Reaction equation

HRID 1768503 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:22][Si:23]([CH3:33])([CH3:32])[C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]O>C(#N)C.C(OCC)C>[CH3:22][Si:23]([CH3:33])([CH3:32])[C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][Br:1]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 54454606[2-(Trimethylsilyl)phenyl]methanol

Product 1

HCID 14908452[2-(Bromomethyl)phenyl](trimethyl)silane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

Bromine (1.07 g, 6.7 mmol) was slowly added to a cooled solution of triphenylphosphine (1.83 g, 7.0 mmol) in acetonitrile to maintain a temperature less than or equal to 5° C. A solution of 2-(trimethylsilyl)benzyl alcohol in acetonitrile (10 mL) was slowly introduced and the resulting mixture was allowed to warm to room temperature and stir. Thin layer chromatography after 20 min indicated no starting material remained. The mixture was diluted with diethyl ether (50 mL) and washed with H2O (two-times with 20 mL), dried (MgSO4) and concentrated under vacuum to yield an opaque oil, 2.5 g. Purification by column chromatography (100 g SiO2 eluting with hexanes) provided the product of Step C as a clear, colorless oil, 1.12 g; (69%); IR (neat): 2954, 1250, 1216, 1110 cm-1 ; 1H NMR (CDCl3); δ7.5-7.3 (m,4H), 4.6 (s,2H), 0.4 (s,9H).

Workup

  1. temperatureto maintain a temperature less than or equal to 5° C
  2. washwashed with H2O (two-times with 20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. customto yield an opaque oil, 2.5 g
  6. customPurification by column chromatography (100 g SiO2 eluting with hexanes)

Sources & evidence

ORD record
ord-a62493e55c474a6fbc6eed8116436e04
Source dataset
uspto-grants-1995_01
Patent number
USH0001401

Reaction notes

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