Trifluoroacetic acid → HCID 86698867, compound

HRID 1054902Notes

Reaction equation

HRID 1054902 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:31])[CH2:10][O:11]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:31])[CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698866HCID 86698866, compound

Product 1

HCID 86698867HCID 86698867, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-iodo-4-{[1-(trityloxy)propan-2-yl]oxy}benzene (350 mg, 0.67 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (5 mL). The mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated and purified by combiflash (petroleum ether:ethyl acetate=10:1 to 4:1) to give the title compound (100 mg, 55%) as a white solid, which was used into next step directly. 1H NMR (400 MHz, CDCl3) ppm 7.55 (d, 2H), 6.72 (d, 2H), 4.45 (m, 1H), 3.70 (m, 2H), 1.96 (t, 1H), 1.25 (d, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by combiflash (petroleum ether:ethyl acetate=10:1 to 4:1)

Sources & evidence

ORD record
ord-32e15a809586407c96d632393e44d179
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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