Diethyl Ether → (5-Bromo-2-((4'-chloro-2-fluoro-5-methoxy-3'-methyl-[1,1'-biphenyl]-4-yl)amino)phenyl)methanol

HRID 1504452Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH3:28])[CH:22]=3)=[C:15]([F:29])[CH:14]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH3:28])[CH:22]=3)=[C:15]([F:29])[CH:14]=2)=[C:6]([CH2:7][OH:8])[CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with methyl 5-bromo-2-((4′-chloro-2-fluoro-5-methoxy-3′-methyl-[1,1′-biphenyl]-4-yl)amino)benzoate (7.15 g, 14.94 mmol). A septum was attached and the flask was flushed with N2. To the flask was added THF (149 ml) and the solution was cooled to 0° C. An ethyl ether solution of lithium aluminum hydride solution (17.92 ml, 17.92 mmol, 1M) was added dropwise via syringe to generate an orange solution. After 10 minutes, water (0.68 mL), and 15% NaOH (0.68 mL) were added. The mixture was stirred 10 minutes and then an additional 2.0 mL water was added to generate a white precipitate. The mixture was filtered through a plug of silica and the mother liquor was concentrated to give a tan foam. This was used in the next reaction without further purification. (ESI) 450.0 (M−H)−.

Workup

customthe flask was flushed with N2
additionTo the flask was added THF (149 ml)
filtrationThe mixture was filtered through a plug of silica
concentrationthe mother liquor was concentrated
customto give a tan foam
customThis was used in the next reaction without further purification

Sources & evidence

ORD record: ord-3fd90856349741ddb5328bcc3bc9faf7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212182B2

Reaction notes

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