2,2,2-Trifluoroethanol → 1-Bromo-4-chloro-5-(4-ethylbenzyl)-2-(2-(2,2,2-trifluoroethoxy)ethoxy)benzene

HRID 1175327Notes

Reaction equation

HRID 1175327 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([Cl:21])=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].[F:22][C:23]([F:27])([F:26])[CH2:24]O>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=2)[C:9]([Cl:21])=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][O:7][CH2:24][C:23]([F:27])([F:26])[F:22]

Participants

4

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 595577142-(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol

Product 1

HCID 595577181-Bromo-4-chloro-5-(4-ethylbenzyl)-2-(2-(2,2,2-trifluoroethoxy)ethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol (AU) (0.53 g, 1.4 mmol) in anhydrous CH2Cl2 (4 mL), was added 2,2,2-trifluoroethanol (0.43 g, 4.3 mmol) and triphenylphosphine polystyrene resin (0.57 g, 2.2 mmol). The resulting mixture was stirred overnight at room temperature, after which it was heated for 2 h at 45° C. The mixture was absorbed onto Celite and purified using silica gel column chromatography eluting with a gradient of EtOAc in hexanes to give intermediate BR. 1H-NMR (CDCl3, 300 MHz) δ 7.36 (s, 1H), 7.14 (m, 4H), 6.94 (s, 1H), 4.17-4.01 (m, 8H), 2.67 (q, J=7.5 Hz, 2H), 1.27 (t, J=7.5 Hz, 3H).

Workup

  1. temperatureafter which it was heated for 2 h at 45° C
  2. customThe mixture was absorbed onto Celite
  3. custompurified
  4. washeluting with a gradient of EtOAc in hexanes
  5. customto give intermediate BR

Sources & evidence

ORD record
ord-4d3e042f88c744e483398497e58a9ced
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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