Cesium carbonate → HCID 58086339, compound

HRID 1908084Notes

Reaction equation

HRID 1908084 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-8b7d4739fd3549abb4794d9640891d89
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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