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Dimethyl Sulfoxide → 4-Bromo-4'-(trifluoromethoxy)biphenyl-3-carbaldehyde

HRID 1880568
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HRID 1880568 반응식
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]
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참가 물질

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반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67485623[4-Bromo-4'-(trifluoromethoxy)biphenyl-3-yl]methanol

생성물 1

HCID 866212244-Bromo-4'-(trifluoromethoxy)biphenyl-3-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매
2회

실험 절차

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

후처리

  1. additionwas added
  2. customThe solution was partitioned between aqueous saturated NH4Cl and DCM
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-abe076a363ca43a8a40e59bf3be8bd92
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318760B2

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