3-Bromo-5-chloroaniline → 3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 1043709Notes

Reaction equation

HRID 1043709 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].ClC1C([B:18]2[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]2)=CC=CC=1N>>[Cl:9][C:7]1[CH:6]=[C:4]([CH:3]=[C:2]([B:18]2[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]2)[CH:8]=1)[NH2:5]

Participants

3

Reactant 2

HCID 30847093-Bromo-5-chloroanilineHCID 581644322-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

Product 1

HCID 510345763-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineYield 48%

Procedure

This material was prepared from 3-bromo-5-chloroaniline following a similar procedure used for SM-9, step 3. The crude product was purified by flash chromatography (RediSep Cyano®, Teledyne ISCO, 0-50% EtOAc in hexanes) to afford 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (48%) as a pale orange solid: LCMS (m/z) 172.1 (MH+), tR=0.33 minute.

Workup

  1. customThe crude product was purified by flash chromatography (RediSep Cyano®, Teledyne ISCO, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d0b136ac24b748c4a69835d2ed83cd31
Source dataset
uspto-grants-2013_10
Patent number
US08563553B2

Reaction notes

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