Water → HCID 58703550, compound

HRID 1179464Notes

Reaction equation

HRID 1179464 reaction equation
C1([Li])C=CC=CC=1.Br[C:9]1[CH:14]=[C:13]([O:15][CH2:16][O:17][CH3:18])[CH:12]=[C:11]([Br:19])[C:10]=1[O:20][CH2:21][O:22][CH3:23].CN([CH:27]=[O:28])C.O>C1CCCCC1.CCOCC.C1COCC1>[Br:19][C:11]1[C:10]([O:20][CH2:21][O:22][CH3:23])=[C:9]([CH:14]=[C:13]([O:15][CH2:16][O:17][CH3:18])[CH:12]=1)[CH:27]=[O:28]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 21364580HCID 21364580, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 58703550HCID 58703550, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21895417Cyclohexane diethyletherSolvent

Procedure

Add a solution of phenyllithium (7.80 mL of a 1.8 M solution in cyclohexane-Et2O (70:30), 14.04 mmol) over 15 seconds to a −78° C. solution of 1,3-dibromo-2,5-bis-methoxymethoxy-benzene (5.00 g, 14.04 mmol) in THF (100 mL). After stirring the reaction for 15 minutes, add DMF (2.17 mL, 28.08 mmol) and stir the reaction for 1 hour. Pour the reaction into H2O (150 mL) and extract with EtOAc (2×100 mL). Combine the organic extracts, wash with brine, dry (MgSO4), filter and concentrate. Purify the crude material using silica gel chromatography, eluting with Hex:EtOAc (80:20) to afford the subtitled product (3.00 g, 70%) as an oil. 1H NMR (CDCl3) δ 3.47 (s, 3H), 3.61 (s, 3H), 5.14 (s, 2H), 5.16 (s, 2H), 7.45 (d, J=3.0 Hz, 1H), 7.53 (d, J=3.1 Hz, 1H), 10.29 (s, 1H).

Workup

  1. customthe reaction for 15 minutes
  2. stirringstir
  3. customthe reaction for 1 hour
  4. additionPour
  5. extractionextract with EtOAc (2×100 mL)
  6. washCombine the organic extracts, wash with brine
  7. dry with materialdry (MgSO4)
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify the crude material
  11. washeluting with Hex

Sources & evidence

ORD record
ord-eaa75f200f204571b80db8c27a922bb1
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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