Formaldehyde → HCID 86650250, compound

HRID 221672Notes

Reaction equation

HRID 221672 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12]=[O:13].[CH3:14]CN(CC)CC.[OH2:21]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([N+:9]([O-:11])=[O:10])([CH2:14][OH:21])[CH2:12][OH:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 8471TriethylamineHCID 214681911-Bromo-3-(nitromethyl)benzene

Product 1

HCID 86650250HCID 86650250, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 1-bromo-3-nitromethyl-benzene (6.82 g, 31.6 mmol), formaline (35%, 5.22 ml, 66.3 mmol) and Et3N (2.2 ml, 15.78 mmol) was heated at 50° C. for 1 h, diluted with water and extracted with TBME. The organic phase was washed with brine, dried with MgSO4 and evaporated. The residue was crystallized from TBME/hexane to yield the title compound in the form of a colourless solid. TLC (hexane/EtOAc=2:1): Rf=0.2; HPLC: RtH2=3.117 min; 1H-NMR (400 MHz, CD3OD): 7.61-7.54 (m, 2H), 7.39-7.34 (m, 2H), 4.40 (d, 2H), 4.35 (d, 2H); MS: 298, 300 [(M+Na)+].

Workup

  1. extractionextracted with TBME
  2. washThe organic phase was washed with brine
  3. dry with materialdried with MgSO4
  4. customevaporated
  5. customThe residue was crystallized from TBME/hexane

Sources & evidence

ORD record
ord-2393a121420a4441b46ba6760f5ede1e
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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