1-(Bromomethyl)-4-(trifluoromethyl)benzene → HCID 71186594, compound

HRID 712864Notes

Reaction equation

HRID 712864 reaction equation
FC(F)(F)C(O)=O.[CH2:8]1[C:10]2([CH2:15][CH2:14][NH:13][CH:12]([C:16]([NH:18][C:19]3([C:22]4[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=4)[CH2:21][CH2:20]3)=[O:17])[CH2:11]2)[CH2:9]1.[F:32][C:33]([F:43])([F:42])[C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1>CC#N>[F:32][C:33]([F:42])([F:43])[C:34]1[CH:41]=[CH:40][C:37]([CH2:38][N:13]2[CH2:14][CH2:15][C:10]3([CH2:9][CH2:8]3)[CH2:11][CH:12]2[C:16]([NH:18][C:19]2([C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=3)[CH2:20][CH2:21]2)=[O:17])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 71186605HCID 71186605, compound

Product 1

HCID 71186594HCID 71186594, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of methyl 4-(1-(6-azaspiro[2.5]octane-5-carboxamido)cyclopropyl)benzoate 2,2,2-trifluoroacetate (D89) (27 g, 61.03 mmol) in dry MeCN (900 ml) Cs2CO3 (39.7 g, 122.05 mmol) and a solution of 4-(trifluoromethyl)-benzylbromide (14.6 g, 61.03 mmol) in MeCN (50 ml) were added in sequence. The mixture was stirred at RT for 18 hrs. The solid was filtered off and solvents were evaporated. The residue was ri-dissolved in DCM (200 ml) and washed with H2O (3×100 ml) and NaCl sat. sol (50 ml). The organic phases were dried over Na2SO4 and evaporated to afford a white solid, which was triturated in cyclohexane to afford the title compound (D123) (19.7 g).

Workup

  1. filtrationThe solid was filtered off
  2. customsolvents were evaporated
  3. dissolutionThe residue was ri-dissolved in DCM (200 ml)
  4. washwashed with H2O (3×100 ml) and NaCl sat. sol (50 ml)
  5. dry with materialThe organic phases were dried over Na2SO4
  6. customevaporated
  7. customto afford a white solid, which
  8. customwas triturated in cyclohexane

Sources & evidence

ORD record
ord-b8c9a8d8d6b24af4be611df8efba5c97
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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