Tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoate → Tert-butyl 5-cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)-methoxy)benzoate

HRID 1849796Notes

Reaction equation

HRID 1849796 reaction equation
[C:1]12(COC3C(Cl)=CC(C(OC(C)(C)C)=O)=C(F)C=3)[CH2:7][CH:6]1CCCC2.Cl[C:26]1[C:27]([O:40][CH2:41][C:42]2([F:48])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[CH:28][C:29]([F:39])=[C:30]([CH:38]=1)[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>>[CH:1]1([C:26]2[C:27]([O:40][CH2:41][C:42]3([F:48])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[CH:28][C:29]([F:39])=[C:30]([CH:38]=2)[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 86703665Tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoateHCID 86703680Tert-butyl 5-chloro-2-fluoro-4-((1-fluorocyclohexyl)methoxy)benzoate

Product 1

HCID 86703679Tert-butyl 5-cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)-methoxy)benzoate

Procedure

Following the procedure as described in Example 342 Step 4 and making variations as required to replace tert-butyl 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-chloro-2-fluorobenzoate with tert-butyl 5-chloro-2-fluoro-4-((1-fluorocyclohexyl)methoxy)benzoate, the title compound was obtained as a colorless gum (1.60 g, 90%): 1H NMR (300 MHz, CDCl3) δ 7.38 (d, J=8.4 Hz, 1H), 6.49 (d, J=12.5 Hz, 1H), 3.93 (d, J=17.8 Hz, 2H), 2.04-1.87 (m, 4H), 1.73-1.55 (m, 6H), 1.54 (s, 9H), 1.36-1.20 (m, 3H), 0.91-0.80 (m, 2H), 0.65-0.57 (m, 2H).

Sources & evidence

ORD record
ord-744129e0d1de4f748a3949b1a62132ac
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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