N-bromobutanimide → [2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanol

HRID 1798078Notes

Reaction equation

HRID 1798078 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:15][OH:16])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.C1C(=O)N([Br:24])C(=O)C1>CN(C=O)C.C(OCC)(=O)C>[Br:24][C:6]1[C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][C:9]([O:11][CH2:12][O:13][CH3:14])=[CH:8][C:7]=1[CH2:15][OH:16]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 104437513,5-Bis(methoxymethoxy)benzylalcohol

Product 1

HCID 10957768[2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanolYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3,5-bis-methoxymethoxy-phenyl)-methanol (9.16 g, 40.2 mmol) in DMF (40 mL) was treated with NBS (7.51 g, 42.2 mmol) at room temperature and the mixture was stirred at same temperature for 30 min. The residue was diluted with ethyl acetate and washed with brine. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=1:1) to afford the title compound (10.2 g, 83%). 1H NMR (300 MHz, CDCl3) δ 6.91 (s, 1H), 6.81 (s, 1H), 5.24 (s, 2H), 5.17 (s, 2H), 4.72 (d, J=6.3 Hz, 2H), 3.52 (s, 3H), 3.47 (s, 3H), 2.05 (t, 1H).

Workup

  1. washwashed with brine
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-661360b424bb463fbcd39e1ef42a0a26
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…