2-(Dimethylamino)ethanol → [2-(3-Bromophenoxy)ethyl]dimethylamine

HRID 2196678Notes

Reaction equation

HRID 2196678 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Br:15][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23]

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 115633-BromophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 413371[2-(3-Bromophenoxy)ethyl]dimethylamineYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl diazene-1,2-dicarboxylate (1.1 eq.) was added dropwise to a 0° C. solution of 3-bromophenol (1.155 g, 6.68 mmol, 1.0 eq.), 2-(dimethylamino)ethanol (1.1 eq.) and triphenylphosphine (1.1 eq.) in THF (20 mL). The mixture was allowed to warm to room temperature over 16 hours, and then the volatiles were removed under reduced pressure. The resulting residue was partitioned between EtOAc (20 mL) and 1N HCl (20 mL), and the aqueous layer was collected and washed with EtOAc. The aqueous layer was neutralized with saturated NaHCO3 (50 mL), extracted with EtOAc, and dried (MgSO4). Purification via silica chromatography (eluting with 4% MeOH/DCM) afforded 2-(3-bromophenoxy)-N,N-dimethylethanamine (1.032 g, 63%) as an oil.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe resulting residue was partitioned between EtOAc (20 mL) and 1N HCl (20 mL)
  3. customthe aqueous layer was collected
  4. washwashed with EtOAc
  5. extractionextracted with EtOAc
  6. dry with materialdried (MgSO4)
  7. customPurification
  8. washvia silica chromatography (eluting with 4% MeOH/DCM)

Sources & evidence

ORD record
ord-0b91ab798f87498e993972c476e3e9f4
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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