Trifluoroacetic acid → 2-(2-Aminoethyl)-4-bromophenyl benzyl ether

HRID 1006045Notes

Reaction equation

HRID 1006045 reaction equation
[BH4-].[Na+].FC(F)(F)C(O)=O.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[CH2:25][C:26]#[N:27])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[CH2:25][CH2:26][NH2:27])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 226754674-Bromo-2-cyanomethylphenyl benzyl ether

Product 1

HCID 179382632-(2-Aminoethyl)-4-bromophenyl benzyl etherYield 108.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of NaBH4 (6.0 g) in THF (100 ml) was added dropwise trifluoroacetic acid (18 ml) at 0° C. (ice bath). 4-Bromo-2-cyanomethylphenyl benzyl ether (10 g) was added and the mixture stirred at ambient temperature for 18 hours. The reaction was quenched with water (100 ml), the pH adjusted to 13 with 2N aqueous NaOH solution, and extracted with diethyl ether. The diethyl ether extracts were dried (MgSO4) and evaporated to give 2-(2-aminoethyl)-4-bromophenyl benzyl ether (11.0 g) as a yellow gum.

Workup

  1. customThe reaction was quenched with water (100 ml)
  2. extractionextracted with diethyl ether
  3. dry with materialThe diethyl ether extracts were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-42772ebd4df24af5b2fcde9907289aec
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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