Triphenylphosphine → HCID 68944646, compound

HRID 242708Notes

Reaction equation

HRID 242708 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1[CH2:5][Br:6])[CH3:2].C1([P:18](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Br-:6].[CH2:1]([C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1[CH2:5][PH3+:18])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 529879492-(Bromomethyl)-1-ethyl-3-methylbenzene

Product 1

HCID 68944646HCID 68944646, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-ethyl-6-methylbenzylbromide (0.432 g, 2.03 mmol) in toluene (10 mL) was added triphenylphosphine (0.6018 g, 2.29 mmol). The mixture was heated at 100° C. for 4 h. After cooling to room temperature, the precipitate was collected by filtration and washed with toluene to give 2-ethyl-6-methylbenzylphosphonium bromide as a solid. Yield (0.958 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ 7.90-7.92 (m, 3H), 7.69 (ddd, J=8.4, 8.4, 3.6 Hz, 6H), 7.49-7.55 (m, 6H), 7.20 (ddd, J=7.6, 7.6, 2.8 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 6.94 (d, J=7.6 Hz, 1H), 4.91 (d, J=14.7 Hz, 2H), 2.05 (q, J=6.7 Hz, 2H), 1.75 (s, 3H), 0.78 (t, J=6.7 Hz, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with toluene

Sources & evidence

ORD record
ord-085cd18d9c554592bb6208dd03845b20
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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