4-Chlorobenzoyl chloride → HCID 68494851, compound

HRID 453610Notes

Reaction equation

HRID 453610 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:9]=[C:8]([C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([Cl:17])=[CH:19][CH:20]=2)[S:7][C:6]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 68496531HCID 68496531, compound

Product 1

HCID 68494851HCID 68494851, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.05 g (0.22 mmol) of 15 and 27 uL (0.22 mmol) of 4-chlorobenzoyl chloride in 5 mL of dry CH2Cl2 was added 15 mg (0.11 mmol) of AlCl3 in three portions at room temperature. The resulting mixture was stirred overnight. The reaction mixture was slowly poured onto 5 g of ice and allowed to warm to room temperature. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/Hex 1:9) to give 0.04 g (50%) of [5-(4-chlorobenzoyl)-2-phenylthiophene-3-yl]acetic acid methyl ester as a white solid: 1H NMR (600 MHz, CDCl3) δ 7.84 (d, J=8.2 Hz, 2H), 7.61 (s, 1H), 7.50-7.43 (m, 3H), 3.71 (s, 3H), 3.67 (s, 2H); 13C NMR (150 MHz, CDCl3) δ 186.5, 171.1, 150.1, 140.8, 138.6, 137.3, 136.2, 132.6, 130.5, 129.2, 128.9, 128.8, 128.7, 52.2, 34.1; IR (KBr) cm−1 2949, 1737, 1623; LREIMS C20H15ClO3S requires 370.04. Found: 370 ([M+], 100%), 310 (40%), 139 (59%).

Workup

  1. dry with materialThe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (EtOAc/Hex 1:9)

Sources & evidence

ORD record
ord-fc8e9643ebdb452193f153b47f2e6ccb
Source dataset
uspto-grants-2013_07
Patent number
US08492428B2

Reaction notes

Loading…