[4-Bromo-3-(2,2,2-trifluoroethyl)phenyl]methanol → 4-Bromo-3-(2,2,2-trifluoroethyl)benzaldehyde

HRID 63862Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[CH2:10][C:11]([F:14])([F:13])[F:12].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[CH2:10][C:11]([F:12])([F:13])[F:14]

Participants

Conditions

Temperature: 25 °C

Procedure

Into a 100-mL round-bottom flask, was placed a solution of [4-bromo-3-(2,2,2-trifluoroethyl)phenyl]methanol (800 mg, 2.97 mmol, 1.00 equiv) in dichloromethane (20 mL), PCC (1.3 g, 6.03 mmol, 2.00 equiv). The resulting solution was stirred for 3 h at 25° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30-1:10). This resulted in 700 mg (88%) of 4-bromo-3-(2,2,2-trifluoroethyl)benzaldehyde as yellow oil.

Workup

customInto a 100-mL round-bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 700 mg (88%) of 4-bromo-3-(2,2,2-trifluoroethyl)benzaldehyde as yellow oil

Sources & evidence

ORD record: ord-2c2dff000cae4b03969d341c04b6df6a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447084B2

Reaction notes

Loading…