Dimethyl Sulfoxide → 4-Bromo-4'-(trifluoromethoxy)biphenyl-3-carbaldehyde
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)=[CH:14][C:13]=1[CH2:29][OH:30].C(N(CC)CC)C>C(Cl)Cl>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:22][CH:23]=2)=[CH:14][C:13]=1[CH:29]=[O:30]Participants
Procedure
DMSO (0.69 mL, 9.72 mmol) was added dropwise to oxalyl chloride (0.42 mL, 4.86 mmol) in 4 mL DCM at −78° C. After 20 minutes a DCM solution (6 mL) of the intermediate from Step C (1.2 g, 3.47 mmol) was added dropwise. After stirring for 15 minutes at −78° C. triethylamine (2.42 mL, 17.35 mmol) was added. The reaction mixture was then allowed to warm to room temperature. The solution was partitioned between aqueous saturated NH4Cl and DCM. The organic phase was washed with water, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 10.43 (s, 1H); 8.12 (d, J=2.4 Hz, 1H); 7.75 (d, J=8.6 Hz, 1H); 7.67-7.65 (m, 1H); 7.63 (d, J=8.5 Hz, 2H); 7.34 (d, J=8.5 Hz, 2H). LCMS1 4.09 min. (M+H)=345
Workup
- additionwas added
- customThe solution was partitioned between aqueous saturated NH4Cl and DCM
- washThe organic phase was washed with water, brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-abe076a363ca43a8a40e59bf3be8bd92
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318760B2
Reaction notes
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