Triphenylphosphine → HCID 86698221, compound

HRID 882559Notes

Reaction equation

HRID 882559 reaction equation
[CH2:1]([O:3][CH2:4][O:5][C:6]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8]O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:41])C(=O)C1>C(Cl)Cl>[CH2:1]([O:3][CH2:4][O:5][C:6]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][Br:41])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 86698220HCID 86698220, compound

Product 1

HCID 86698221HCID 86698221, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(ethoxymethoxy)-3-methylbenzyl alcohol (Ib) (2.67 g, 13.6 mmol) and triphenylphosphine (5.35 g, 20.4 mmol) in CH2Cl2 (70 mL) was added NBS (3.63 g, 20.4 mmol) at RT. The reaction was stirred at RT for 2 h, and quenched with water (15 mL). The product was extracted with CH2Cl2 (3×30 mL). The combined organic extracts were washed with water (30 mL), brine (30 mL), dried over Na2SO4, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (hexane/ethyl acetate=10:1, v/v) yielded the compound IIb as a colorless oil (1.56 g, 77%).

Workup

  1. customquenched with water (15 mL)
  2. extractionThe product was extracted with CH2Cl2 (3×30 mL)
  3. washThe combined organic extracts were washed with water (30 mL), brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by flash column chromatography (hexane/ethyl acetate=10:1

Sources & evidence

ORD record
ord-3951e115e6f944df8fab451cc20daecc
Source dataset
uspto-grants-2015_03
Patent number
US08993804B2

Reaction notes

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