Ammonium Hydroxide → HCID 58674637, compound

HRID 1994131Notes

Reaction equation

HRID 1994131 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].B(Br)(Br)Br.[NH4+].[OH-]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[C:22]([F:23])([F:24])[F:25]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 58674517HCID 58674517, compound

Product 1

HCID 58674637HCID 58674637, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-4-(4-methoxyphenyl)butanamide (460 mg, 1.23 mmol) in DCM (6 mL) at 0° C. was added BBr3 (1.0 M in DCM, 0.40 mL, 0.4 mmol) dropwise. The solution was allowed to warm to rt. Upon reaction completion, the solution was poured onto ice and neutralized with NH4OH. The yellow solid was filtered off and rinsed with hexanes and Et2O to give the product as a white solid (356 mg, 81%). LCMS, AA: Rt=1.94 min, [MH− 356.1].

Workup

  1. customUpon reaction completion
  2. filtrationThe yellow solid was filtered off
  3. washrinsed with hexanes and Et2O

Sources & evidence

ORD record
ord-20b71a4db2ea43b1b3e992df0a9901a8
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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