Dichloromethane → HCID 18786749, compound

HRID 1107221Notes

Reaction equation

HRID 1107221 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)[CH2:5][F:6].C(Cl)Cl.[OH-].[Na+]>CO>[NH2:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([I:1])[CH:9]=1)[CH2:5][F:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 18786757HCID 18786757, compound

Product 1

HCID 18786749HCID 18786749, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3-iodo-5-nitrobenzyl fluoride (9.2 g, 32.7 mmol) described in Step C, in methanol (311 mL) was treated with TiCl3 (311 mL, >10 wt. % in 20-30 wt % HCl) and stirred at room temperature for 20 minutes. The reaction was poured into a separatory funnel containing 95:5 CH2Cl2 :MeOH and the aqueous layer was made basic with 15% aq. NaOH. The layers were separated and the aqueous layer was extracted with 95:5 CH2Cl2 :MeOH. The organic layers were combined, dried (MgSO4), filtered and concentrated to give an orange semi-solid. Purification by flash chromatography (3:1 to 1:1 hexane:methylene chloride) provided 3-amino-5-iodobenzyl fluoride as a tan solid: mp 48.5-50° C.

Workup

  1. additionThe reaction was poured into a separatory funnel
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 95:5 CH2Cl2
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an orange semi-solid
  8. customPurification by flash chromatography (3:1 to 1:1 hexane:methylene chloride)

Sources & evidence

ORD record
ord-abbd2f201dbb49339bce489d765fcae3
Source dataset
uspto-grants-2000_05
Patent number
US06060038

Reaction notes

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