Carbon Tetrachloride → 3-(Chloromethyl)-5-(4-fluorophenyl)-1,2-oxazole

HRID 913643Notes

Reaction equation

HRID 913643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH2:13]O)[CH:9]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:35]>C(Cl)Cl>[Cl:35][CH2:13][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:12][N:11]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 16217812[5-(4-Fluorophenyl)-1,2-oxazol-3-yl]methanol

Product 1

HCID 166414733-(Chloromethyl)-5-(4-fluorophenyl)-1,2-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of [5-(4-fluorophenyl)-3-isoxazolyl]methanol (0.2 g, 1.04 mmol) in 5 mL of CCl4 and 0.5 mL of CH2Cl2 was added Ps-triphenylphosphine (3 mmol/g, 0.69 g, 2.08 mmol), and the mixture was heated at 65° C. for 3 h. Upon cooling, the resin was filtered off and washed with CH2Cl2 and EtOAc. The filtrate was concentrated to dryness to afford the title compound as a light brown solid, which was used in the next reaction without further purification: 1H NMR (400 MHz, CDCl3) δ 7.75 (t, J=6.6 Hz, 2H), 7.14 (t, J=8.3 Hz, 2H), 6.55 (s, 1H), 4.6 (s, 2H).

Workup

  1. temperatureUpon cooling
  2. filtrationthe resin was filtered off
  3. washwashed with CH2Cl2 and EtOAc
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a96182a7c4e842f2838d349e2917c612
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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