Ammonium Chloride → HCID 59557719, compound

HRID 1175325Notes

Reaction equation

HRID 1175325 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[OH:18].CC(C)([O-])C.[K+].FC(F)(F)S(O[CH2:31][CH2:32][O:33][C:34]([F:37])([F:36])[F:35])(=O)=O.[NH4+].[Cl-]>CC#N>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[O:18][CH2:31][CH2:32][O:33][C:34]([F:37])([F:36])[F:35]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 106351812-(Trifluoromethoxy)ethyl trifluoromethanesulfonateHCID 23665647Potassium tert-butoxideHCID 59557707HCID 59557707, compound

Product 1

HCID 59557719HCID 59557719, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromo-5-chloro-4-(4-ethylbenzyl)phenol (AT) (0.12 g, 0.38 mmol) in anhydrous CH3CN (4 mL), was added potassium tert-butoxide [1.0 M solution in tert-butanol] (380 μL, 0.38 mmol) followed by 2-(trifluoromethoxy)ethyl trifluoromethanesulfonate (0.10 g, 0.38 mmol) [prepared as described in the Journal of Organic Chemistry, 2001, 66, 1061-1063]. The reaction mixture was stirred for 15 h at room temperature, after which saturated NH4Cl was added and the mixture was partitioned between EtOAc and brine. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by preparative TLC to give intermediate BP (0.06 g, 36%). 1H-NMR (CDCl3, 300 MHz) δ 7.31 (s, 1H), 7.10 (m, 4H), 6.89 (s, 1H), 4.31 (m, 2H), 4.20 (m, 2H), 3.96 (s, 2H), 2.61 (q, J=7.5 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H).

Workup

  1. customprepared
  2. customthe mixture was partitioned between EtOAc and brine
  3. dry with materialThe organic layer was dried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC
  7. customto give intermediate BP (0.06 g, 36%)

Sources & evidence

ORD record
ord-e581e6b0956e480bb6cac81324d85872
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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