Water → HCID 59653567, compound

HRID 2052767Notes

Reaction equation

HRID 2052767 reaction equation
C(N(C(C)C)C(C)C)C.[Br:10][C:11]1[C:16]([OH:17])=[C:15]([F:18])[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][CH:12]=1.[CH3:24][O:25][CH2:26][CH2:27][O:28][CH2:29]Cl.O>ClCCl>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:15]([F:18])[C:16]=1[O:17][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 58687484HCID 58687484, compound

Product 1

HCID 59653567HCID 59653567, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60.4 ml (0.355 mol) of ethyldiisopropylamine were added with ice-cooling to 77.4 g (0.294 mol) of 6-bromo-3-butoxy-2-fluorophenol dissolved in 500 ml of dichloromethane, 40.3 ml (0.355 mol) of 2-methoxyethoxymethyl chloride were added dropwise, and the mixture was left to stirr overnight at room temperature. The batch was hydrolysed using water, extracted with dichloromethane and evaporated, and the crude product was filtered through silica gel with n-heptane/MTB ether (3:1), giving 103 g (99%) of 1-bromo-4-butoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzene as a yellow oil.

Workup

  1. waitthe mixture was left
  2. extractionextracted with dichloromethane
  3. customevaporated
  4. filtrationthe crude product was filtered through silica gel with n-heptane/MTB ether (3:1)

Sources & evidence

ORD record
ord-b32849e5578f4751bd1d4329ef8b3513
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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