Cyclopropanemethanol → 2-Bromo-1-(cyclopropylmethoxy)-4-(ethylsulfonyl)benzene

HRID 575690Notes

Reaction equation

HRID 575690 reaction equation
C1(CO)CC1.C[O-].[Na+].[CH3:9][N:10]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]1=[O:29].[Br:30][C:31]1[CH:36]=[C:35]([S:37]([CH2:40][CH3:41])(=[O:39])=[O:38])[CH:34]=[CH:33][C:32]=1[O:42][CH2:43][CH:44]1[CH2:46][CH2:45]1>>[Br:30][C:31]1[CH:36]=[C:35]([S:37]([CH2:40][CH3:41])(=[O:39])=[O:38])[CH:34]=[CH:33][C:32]=1[O:42][CH2:43][CH:44]1[CH2:46][CH2:45]1.[CH:44]1([CH2:43][O:42][C:32]2[CH:31]=[CH:36][C:35]([S:37]([CH2:40][CH3:41])(=[O:39])=[O:38])=[CH:34][C:33]=2[C:18]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:11](=[O:29])[N:10]([CH3:9])[CH:19]=2)[CH2:45][CH2:46]1

Participants

6

Reactant 4

HCID 75644CyclopropanemethanolHCID 10942334Sodium MethoxideHCID 896561482-Bromo-1-(cyclopropylmethoxy)-4-(ethylsulfonyl)benzeneHCID 1238019002-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroisoquinolin-1-one

Product 2

HCID 896561482-Bromo-1-(cyclopropylmethoxy)-4-(ethylsulfonyl)benzeneHCID 118021337US10023592, Example 219

Procedure

2-bromo-1-(cyclopropylmethoxy)-4-(ethanesulfonyl)benzene was prepared in a similar manner as Example 79, step 3 except that the alkoxide of cyclopropylmethanol was substituted for sodium methoxide. The title compound of Example 163, step 3 and 2-bromo-1-(cyclopropylmethoxy)-4-(ethanesulfonyl)benzene were reacted in a similar manner as in Example 89, step 2 to give the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 7.83 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.56 (d, J=2.4 Hz, 1H), 7.43 (s, 1H), 7.65 (d, J=8.8 Hz, 1H), 4.02-3.90 (m, 2H), 3.43 (s, 3H), 3.29-3.23 (m, 2H), 2.49-2.44 (m, 4H), 1.61-1.50 (m, 4H), 1.15-1.08 (m, 5H), 0.53-0.51 (m, 2H), 0.29-0.27 (m, 2H). LCMS: 402.0 (M+H)+

Sources & evidence

ORD record
ord-ff88d7673fb047d59387c94a1fa73bee
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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