3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde → HCID 86607717, compound

HRID 1454532Notes

Reaction equation

HRID 1454532 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].CC1(C)C(C)(C)OB([C:32]2[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=2)[CH:35]=[O:36])O1>>[CH:35]([C:34]1[C:37]([O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[C:38]([C:2]2[C:16]([O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:15][CH:14]=[C:4]([CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=2)[CH:39]=[CH:32][CH:33]=1)=[O:36]

Participants

3

Reactant 2

HCID 27605863-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehydeHCID 86607696HCID 86607696, compound

Product 1

HCID 86607717HCID 86607717, compound

Procedure

Proceeding as in Reference 19, but substituting methyl-3-formyl-4-hydroxy-5-bromophenylacetate (2.47 g, 9.0 mmol) and 2-methoxymethoxy-5-fluorophenylboronic acid (2.0 g, 10.0 mmol), gave methyl 5′-fluoro-5-formyl-6-hydroxy-2′-methoxymethoxy-biphenyl-3-yl)-acetate (2.2 g, 70%) as a yellow oil which crystallized overnight Proceeding as in Reference 19, but substituting tert-butyl [3-bromo-4-(2-methoxyethoxymethoxy)-benzyl]carbamate (2.3 g, 5.9 mmol) and 2-2-methoxyethoxymethoxy)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (60 mL, 0.1 M in toluene), gave tert-butyl [3′-formyl-6,2′-bis(2-methoxyethoxymethoxy)biphenyl-3-ylmethyl]carbamate (2.96 g).

Workup

  1. customcrystallized overnight Proceeding as in Reference 19

Sources & evidence

ORD record
ord-e53b58165cf645fe80e7da73ae08a8a4
Source dataset
uspto-grants-2009_01
Patent number
US07479502B2

Reaction notes

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