Triphenylphosphine → HCID 86698222, compound

HRID 882560Notes

Reaction equation

HRID 882560 reaction equation
[CH2:1]([O:3][CH2:4][O:5][C:6]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8]O)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:43])C(=O)C1>ClCCl>[CH2:1]([O:3][CH2:4][O:5][C:6]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][Br:43])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 86698223HCID 86698223, compound

Product 1

HCID 86698222HCID 86698222, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(ethoxymethoxy)-3-isopropylbenzyl alcohol (Ic) (2.04 g, 9.09 mmol) and PPh3 (3.82 g, 14.6 mmol) in dichloromethane (45 mL) was added NBS (2.59 g, 14.6 mmol) in portions at 0° C. The reaction was stirred at 0° C. for 30 min. The reaction was quenched by the addition of water (50 mL). The product was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with water (50 mL), and brine (50 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification of the crude product by flash column chromatography (hexanes/ethyl acetate=10:1, v/v) provided the title compound (2.27 g, 86%) as a colorless oil.

Workup

  1. customThe reaction was quenched by the addition of water (50 mL)
  2. extractionThe product was extracted with CH2Cl2 (3×50 mL)
  3. washThe combined organic extracts were washed with water (50 mL), and brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the crude product by flash column chromatography (hexanes/ethyl acetate=10:1

Sources & evidence

ORD record
ord-f6b22ffe5cc94a4db686d7afec8e6620
Source dataset
uspto-grants-2015_03
Patent number
US08993804B2

Reaction notes

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