3-Bromophenol → ((3-Bromophenoxy)methyl)cycloheptane

HRID 875501Notes

Reaction equation

HRID 875501 reaction equation
[CH:1]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:10][C:11]1[CH:12]=[C:13](O)[CH:14]=[CH:15][CH:16]=1>>[Br:10][C:11]1[CH:16]=[C:15]([CH:14]=[CH:13][CH:12]=1)[O:9][CH2:8][CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 115633-BromophenolHCID 78193Cycloheptanemethanol

Product 1

HCID 67317652((3-Bromophenoxy)methyl)cycloheptane

Procedure

Cycloheptylmethanol was coupled with 3-bromophenol following the method used in Example 10. After concentration under reduced pressure, hexanes was added. The mixture was stirred and sonicated then the precipitate was removed by filtration and the solids washed with hexanes. The combined filtrates were concentrated under reduced pressure. Purification by flash chromatography (10 to 50% EtOAc-hexanes gradient) gave ((3-bromophenoxy)methyl)cycloheptane. (Yield 1.0697 g, 56%): 1H NMR (400 MHz, CDCl3) δ 7.12 (t, J=8.4, 1H), 7.06-7.04 (m, 2H), 6.82 (dq, J=8.0, 1.2, 1H), 3.70 (d, J=6.4, 2H), 1.91-1.98 (m, 1H), 1.81-1.88 (m, 2H), 1.42-1.72 (m, 8H), 1.24-1.34 (m, 2H).

Workup

  1. concentrationAfter concentration under reduced pressure, hexanes
  2. additionwas added
  3. customsonicated
  4. customthe precipitate was removed by filtration
  5. washthe solids washed with hexanes
  6. concentrationThe combined filtrates were concentrated under reduced pressure
  7. customPurification by flash chromatography (10 to 50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-0d2b8d52af8f4c2aab48707eb239b82b
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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