Triphenylphosphine → HCID 24757446, compound

HRID 2251323Notes

Reaction equation

HRID 2251323 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:31]=1[C:37]1[C:41]([CH2:42]O)=[C:40]([CH:44]([CH3:46])[CH3:45])[O:39][N:38]=1>ClCCl>[Cl:9][C:3]1[CH:4]=[C:5]([O:8][CH2:42][C:41]2[C:37]([C:31]3[C:30]([Cl:29])=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:36])=[N:38][O:39][C:40]=2[CH:44]([CH3:46])[CH3:45])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 871844-Amino-3-chlorophenolHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanol

Product 1

HCID 24757446HCID 24757446, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-amino-3-chlorophenol (1.14 g, 7.9 mmol), triphenylphosphine (2.08 g, 7.9 mmol), [3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methanol (2.27 g, 7.9 mmol) in dichloromethane (20 mL) was treated with diisopropylazidodicarboxylate (1.57 mL, 7.9 mmol) dropwise. After stirring at ambient temperature for 16 h, the material was chromatographed on silica gel eluting with dichloromethane. Yield=1.73 g (53%) of 2-chloro-4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}aniline.

Workup

  1. customthe material was chromatographed on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-3fb98365163e4308bc7c0c63446aa146
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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