(4-Bromobiphenyl-2-yl)methanol → 4-Bromobiphenyl-2-carbaldehyde

HRID 1043416Notes

Reaction equation

HRID 1043416 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([CH2:14][OH:15])[CH:3]=1>O.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[O:15])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59266499(4-Bromobiphenyl-2-yl)methanol

Product 1

HCID 543917794-Bromobiphenyl-2-carbaldehydeYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

IBX (7.45 g, 26.6 mmol) was added to (4-bromobiphenyl-2-yl)methanol (3.5 g, 13.30 mmol) in dmso (40 mL) and stirred at 60° C. for 2 hours. The reaction was cooled in an ice bath and diluted with water and diethyl ether. The ether layer was washed with brine, dried over MgSO4, filtered and evaporated to give 4-bromobiphenyl-2-carbaldehyde (3.32 g, 12.71 mmol, 96% yield) as an orange oil. LCMS: rt=1.66 min.; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 uL; wavelength=220. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.29-7.39 (m, 3H) 7.43-7.58 (m, 3H) 7.76 (dd, j=8.16, 2.13 Hz, 1H) 8.15 (d, J=2.01 Hz, 1H) 9.91 (s, 1H).

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. washThe ether layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f7f2cd2c6d2e4d8d8702b128a5af8299
Source dataset
uspto-grants-2013_10
Patent number
US08563505B2

Reaction notes

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