Diethyl Ether → Benzeneethanamine, 3,5-difluoro-4-hydroxy-

HRID 228402Notes

Reaction equation

HRID 228402 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[Cl-].[Cl-].[Cl-].[Al+3].[F:16][C:17]1[CH:22]=[C:21]([CH:23]=[CH:24][N+:25]([O-])=O)[CH:20]=[C:19]([F:28])[C:18]=1[OH:29]>C1COCC1>[NH2:25][CH2:24][CH2:23][C:21]1[CH:20]=[C:19]([F:28])[C:18]([OH:29])=[C:17]([F:16])[CH:22]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 537332062,6-Difluoro-4-(2-nitro-vinyl)-phenol

Product 1

HCID 588802Benzeneethanamine, 3,5-difluoro-4-hydroxy-Yield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium aluminum hydride 1.0M in ether (30 mL, 29.8 mmol) at 0° C. a solution of aluminum trichloride (4.0 g, 29.8 mmol) in THF (40 mL) is added. After 5 min a solution of compound obtained in step 1 above (2.0 g, 9.95 mmol) in THF (40 mL) is added and the reaction is allowed to stir at room temperature overnight. Add water and then 3 N HCL, the aqueous layer is extracted with 3/1 n-butanol/toluene. The combined organic layers are dried over sodium sulfate and concentrated. SCX ion-exchange chromatography afforded 1.50 g (87%) of the title compound. Electrospray MS M+1 ion=174. 1H-NMR (methanol-d4, 200 MHz): 6.95-6.78 (m, 2H), 3.14 (t, 2H, J=7.0 Hz), 2.86 (t, 2H, J=7.3 Hz).

Workup

  1. extractionAdd water and then 3 N HCL, the aqueous layer is extracted with 3/1 n-butanol/toluene
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-90391829eb1f4e31aa97371507b61b97
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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