Dichloromethane → HCID 59654728, compound

HRID 659106

Reaction equation

HRID 659106 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]1([C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34](O)=[O:35])[CH:30]=[CH:31][CH:32]=1.C(Cl)Cl>ClC1C=CC=CC=1Cl>[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34]([C:23]2[O:22][C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:25][CH:24]=2)=[O:35])[CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14812Phosphorus oxide (P4O10)HCID 74653(3-Bromophenyl)acetic acidHCID 5193632-Phenylfuran

Product 1

HCID 59654728HCID 59654728, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Phosphorous pentoxide (2.02 g, 14.20 mmol) suspended in 1,2-dichlorobenzene (60 mL) was added to a mixture of 2-phenyl-furan (23) (500 mg, 2.84 mmol) and 3-bromophenylacetic acid (24) (1.34 g, 6.25 mmol). The reaction mixture was heated to 80° C. for 2 hours and then cooled to ambient temperature. DCM was added, the organic layer washed with water and partially reduced in vacuo. The crude product was purified by Flash Master Jones Chromatography using a 50 g silica cartridge and first eluting with heptane to remove excess 1,2-dichlorobenzene, then 5-10% EtOAc in heptane to give the title compound. Yield: 278 mg, 38%; LC-MS tr 1.73 min; HPLC Purity: 100%; MS (ES+) m/z 341, 343 (M+H)

Workup

  1. temperaturecooled to ambient temperature
  2. washthe organic layer washed with water
  3. customThe crude product was purified by Flash Master Jones Chromatography
  4. washfirst eluting with heptane
  5. customto remove excess 1,2-dichlorobenzene

Sources & evidence

ORD record
ord-16232f9a991840aa9087cb202a425d26
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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