Aluminium lithium hydride → 4-(2-((4-Bromophenyl)amino)ethoxy)phenol

HRID 1053570Notes

Reaction equation

HRID 1053570 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 43326296N-(4-bromophenyl)-2-(4-hydroxyphenoxy)acetamide

Product 1

HCID 717359264-(2-((4-Bromophenyl)amino)ethoxy)phenolYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 7b (80 mg, 0.25 mmol) was dissolved in THF (5 ml). LiAlH4 (30 mg, 0.5 mmol) was added portionwise and the reaction was refluxed for 6 hrs. The reaction was quenched slowly with water, 10% sodium hydroxide, and then water again. The aqueous layer was extracted with EtOAc (2×50 mL). The organic was concentrated to yield compound 7 (10 mg, 0.03 mmol, 13% yield). 1H NMR (CDCl3, 400 MHz) δ 7.29 (m, 2H), 6.80 (q, 4H), 6.56 (d, 2H), 4.81 (broad s, 1H), 4.13 (t, 2H), 3.47 (t, 2H); HRMS (ESI, positive) m/z calcd. for C14H14BrNO2 [M+H]+: 308.0286, found: 308.0261.

Workup

  1. temperaturethe reaction was refluxed for 6 hrs
  2. customThe reaction was quenched slowly with water, 10% sodium hydroxide
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. concentrationThe organic was concentrated

Sources & evidence

ORD record
ord-7dc790868e944bea8fd18ed184c78fcc
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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