Dimethylformamide → HCID 54065830, compound

HRID 363010Notes

Reaction equation

HRID 363010 reaction equation
C([C:3]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6])C.[C:13]([O-])([O-])=O.[Cs+].[Cs+].[C:19]1([CH:25](Br)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+].CN([CH:42]=[O:43])C>>[C:19]1([CH:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:12][C:10]2[CH:11]=[CH:3][C:4]([C:5]([O:43][CH2:42][CH3:13])=[O:6])=[CH:8][CH:9]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 236603BromodiphenylmethaneHCID 17904358HCID 17904358, compound

Product 1

HCID 54065830HCID 54065830, compound

Procedure

Under N2, a mixture of ethyl 4-hydroxybenzoic acid (2.5 g, 15 mmol) 1-1, and Cs2CO3 (5.0 g, 15 mmol) in DMF (50 ml) was stirred at room temperature. After 15 min, diphenylmethyl bromide 1-2 (4.0 g, 16 mmol) was added and then heated at 60° C. After 1 h, saturated Na2CO3 was added and the mixture extracted with EtOAc (3×). The combined extracts were washed with H2O, dried, filtered and concentrated to dryness to yield 1-3.

Workup

  1. temperatureheated at 60° C
  2. waitAfter 1 h
  3. extractionthe mixture extracted with EtOAc (3×)
  4. washThe combined extracts were washed with H2O
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customto yield 1-3

Sources & evidence

ORD record
ord-a57b3f4f5b8145f5832025697cc9b1d8
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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