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

HRID 74329Notes

Reaction equation

HRID 74329 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-d3c8a690dbb645429f6b758516825c7a
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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