(4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol → 4'-Bromo-4-(dimethylamino)biphenyl-2-carbaldehyde

HRID 1043437Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][C:9]=2[CH2:17][OH:18])=[CH:4][CH:3]=1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:17]=[O:18])=[CH:10][C:11]([N:14]([CH3:15])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

IBX (3.29 g, 11.76 mmol) was added to a solution of (4′-bromo-4-(dimethylamino)biphenyl-2-yl)methanol (1.8 g, 5.88 mmol) in dmso (50 mL) and stirred at 40° C. for 3 hours. The reaction was diluted with water and extracted with diethyl ether. The ether layer was dried over MgSO4, filtered and evaporated to give the crude material. The crude product was purified on the Biotage (5-20% EtOAc:Hex) to give 4′-bromo-4-(dimethylamino)biphenyl-2-carbaldehyde (1.25 g, 4.11 mmol, 70% yield) as a yellow solid. 1H NMR (500 MHz, CHLOROFORM-d) δ 2.95-3.13 (m, 6H) 7.01 (dd, J=8.55, 3.05 Hz, 1H) 7.22 (m, 2H) 7.28-7.33 (m, 2H) 7.57 (m, 2H) 9.96 (s, 1H).

Workup

extractionextracted with diethyl ether
dry with materialThe ether layer was dried over MgSO4
filtrationfiltered
customevaporated
customto give the crude material
customThe crude product was purified on the Biotage (5-20% EtOAc:Hex)

Sources & evidence

ORD record: ord-4974b1aeb3d0461487574852b37b97d4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563505B2

Reaction notes

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