Cesium carbonate → HCID 58086339, compound

HRID 2204168Notes

Reaction equation

HRID 2204168 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH2:21][O:22][CH3:23]>CN(C=O)C>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:20][CH2:21][O:22][CH3:23])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 5981552-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 58086339HCID 58086339, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-hydroxy-5-methoxy-benzaldehyde (0.500 g, 2.94 mmol) was dissolved in DMF (2.6 mL) containing Cs2CO3 (2.88 g, 8.82 mmol). 1-Bromo-2-methoxy-ethane (1.23 g, 828 μL, 8.82 mmol) was added and the reaction mixture was allowed to stir for 86 h. The reaction mixture was filtered and the filtrate was evaporated to dryness to give 2-fluoro-5-methoxy-4-(2-methoxyethoxy)benzaldehyde. ESI-MS m/z calc. 228.1, found 229.0 (M+1)+. Retention time: 1.14 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ac37acf963784a7cb1d587f4effbd39b
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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