Dimethylformamide → HCID 54148235, compound

HRID 1466026Notes

Reaction equation

HRID 1466026 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)C)=[CH:4][CH:3]=1.C1C(=O)N([Br:18])C(=O)C1.CN([CH:22]=[O:23])C>C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:22][OH:23])=[CH:4][C:3]=1[Br:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 857534-Amino-alpha-methylbenzenemethanol

Product 1

HCID 54148235HCID 54148235, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-aminophenyl ethanol (34 g, 0.25 mol) and NBS (35 g, 0.20 mol) in DMF (660 mL) was stirred at RT overnight. Then the mixture was diluted with ethyl acetate (2 L), washed with water (300 mL×4), dried over Na2SO4, concentrated in vacuo to give the crude product 2-(4-Amino-3-bromophenyl)ethanol. 1H NMR (400 MHz, CDCl3) δ 7.26 (d, J=1.6 Hz, 1H), 6.93 (d, J=1.6 Hz, 1H), 6.70 (s, 1H), 4.44 (br, 1H), 3.76 (t, J=6.4 Hz, 2H), 2.71 (t, J=6.4 Hz, 2H).

Workup

  1. washwashed with water (300 mL×4)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b24bcdacd4345e19e9c58994f46f604
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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