Anisole → HCID 57753362, compound

HRID 2355696Notes

Reaction equation

HRID 2355696 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[CH2:7][N:6](CC1C=CC(OC)=CC=1)[CH2:5]2.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[CH2:7][NH:6][CH2:5]2

Participants

4

Reactant 2

HCID 7519AnisoleHCID 59382310HCID 59382310, compound

Product 1

HCID 57753362HCID 57753362, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-chloro-6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-1H-isoindole (600 mg) and anisole (0.3 ml) in trifluoroacetic acid (6 ml) was heated at 180° C. (50 W) for 40 minutes in a CEM discover microwave synthesiser. The reaction mixture was evaporated and re-evaporated with toluene. The crude material was partitioned between DCM and water, the aqueous layer washed with DCM (×3) then evaporated and re-evaporated with toluene to give 5-chloro-6-methoxy-2,3-dihydro-1H-isoindole (256 mg) as green crystals. MS: [M+H]+ 184

Workup

  1. customThe reaction mixture was evaporated
  2. customre-evaporated with toluene
  3. customThe crude material was partitioned between DCM and water
  4. washthe aqueous layer washed with DCM (×3)
  5. customthen evaporated
  6. customre-evaporated with toluene

Sources & evidence

ORD record
ord-1fe1683361454dd1b84c37d72d4ab716
Source dataset
uspto-grants-2010_07
Patent number
US07754725B2

Reaction notes

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