4-Aminophenol → HCID 2838541, compound

HRID 906040Notes

Reaction equation

HRID 906040 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:45][C:46]1[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 79724-MethylmorpholineHCID 114644-Bromobenzoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 2838541HCID 2838541, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromobenzoic acid in DMF (0.10 M), 3 eq of NMM, 1.5 eq of Py-BOP and 1.1 eq of 4-aminophenol were added and the mixture was stirred at RT for 20 min. DMF was concentrated in vacuo and the residue diluted with EtOAc and aqueous HCl (1N). The resultant precipitate was filtered off and dried in vacuo to afford the title compound (73%); MS (ES+) m/z 292 (M+H)+, m/z 294 (M+H)+

Workup

  1. concentrationDMF was concentrated in vacuo
  2. additionthe residue diluted with EtOAc and aqueous HCl (1N)
  3. filtrationThe resultant precipitate was filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e9c6648ade194df1b4247a6358f61683
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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