Diethyl Ether → HCID 86623639, compound

HRID 602590Notes

Reaction equation

HRID 602590 reaction equation
Br[C:2]1[CH:7]=[C:6](OC)[CH:5]=[C:4]([Br:10])[CH:3]=1.CN([CH:14]=[O:15])C.[Cl-].[NH4+].C[CH2:19][O:20]CC>>[Br:10][C:4]1([CH:3]=[CH:2][CH:7]=[C:6]([CH:14]=[O:15])[CH2:5]1)[CH:19]=[O:20]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 110218123,5-Dibromoanisole

Product 1

HCID 86623639HCID 86623639, compoundYield 98%

Procedure

step 1—n-BuLi (2.6 mL of a 1.6 M solution, 1.1 equiv) was added slowly to a solution of the 1,3-dibromo-5-methoxy-benzene (1.0 g, 3.8 mmol, CAS Reg. No. 74137-36-3) in Et2O (20 mL) cooled to −78° C. under an N2 atmosphere. The solution was stirred for 45 min, and DMF was added via syringe. The solution was warmed slowly to RT, added to saturated ammonium chloride, and extracted with ether. The organic phase was washed with brine and dried (MgSO4), filtered and evaporated to afford 0.80 g (98%) of 1-bromo-3-formyl-benzaldehyde.

Workup

  1. extractionextracted with ether
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-e7df556da9674cc7a8464a0af6fae88d
Source dataset
uspto-grants-2011_03
Patent number
US07906540B2

Reaction notes

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