2-(3-(Benzyloxy)-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → Methyl 3''-(benzyloxy)-4''-chloro-2,6-dimethoxy-1,1':2',1''-terphenyl-4'-carboxylate

HRID 1040354Notes

Reaction equation

HRID 1040354 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=1[O:20][CH3:21].[CH2:22]([O:29][C:30]1[CH:31]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:34][C:35]=1[Cl:36])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([O:29][C:30]1[CH:31]=[C:32]([C:2]2[C:3]([C:12]3[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=3[O:20][CH3:21])=[CH:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=2)[CH:33]=[CH:34][C:35]=1[Cl:36])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 598468812-(3-(Benzyloxy)-4-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66721235Methyl 2-bromo-2',6'-dimethoxybiphenyl-4-carboxylate

Product 1

HCID 66721104Methyl 3''-(benzyloxy)-4''-chloro-2,6-dimethoxy-1,1':2',1''-terphenyl-4'-carboxylateYield 45.1%

Procedure

According to the method described in example 10.2, starting from 2.79 g (7.94 mmol) of methyl 2-bromo-2′,6′-dimethoxybiphenyl-4-carboxylate and 3.28 g (9.53 mmol) of 2-[3-(benzyloxy)-4-chlorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, we obtain 1.75 g of methyl 3″-(benzyloxy)-4″-chloro-2,6-dimethoxy-1,1′:2′,1″-terphenyl-4′-carboxylate in the form of oil.

Sources & evidence

ORD record
ord-d3054f920e3c405296bb968fa095477e
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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