Dichloromethane → HCID 59820835, compound

HRID 1642211Notes

Reaction equation

HRID 1642211 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[CH:6][CH:5]=1.[Cl-].[NH4+].C(Cl)Cl>C(O)C.O.[Fe]>[F:1][C:2]([F:20])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 59820864HCID 59820864, compound

Product 1

HCID 59820835HCID 59820835, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Trifluoromethoxy-4-(2-nitro-phenoxy)-benzene (HVB01037, 2.1 g, 7.02 mmol) was added to a solution of iron powder (2.15 g, 38.61 mmol) and ammonium chloride (0.27 g, 4.9 mmol) in ethanol (40 ml) and water (4 ml) at reflux. Stirred at reflux for 3 h. Ethanol removed in-vacuo and the residue was extracted with sodium hydrogen carbonate. Organic layers dried over anhydrous magnesium sulphate and evaporated to dryness, to afford a brown oil, 1.57 g, 95%. Rf: 0.6 (DCM) 1HNMR (CDCl3, 270 MHz) δ 3.81 (2H, s, NH2), 6.76 (1H, m, Ar HB), 6.84 (1H, dd, J=1.2, 7.9 Hz, Ar HA), 6.91 (1H, dd, J=1.0, 7.9 Hz, Ar HD), 6.98 (2H, d, J=9.1 Hz, Ar HF), 7.04 (1H, m, Ar HC), 7.18 (2H, d, J=8.7 Hz, Ar HE).

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 3 h
  3. customEthanol removed in-vacuo
  4. extractionthe residue was extracted with sodium hydrogen carbonate
  5. dry with materialOrganic layers dried over anhydrous magnesium sulphate
  6. customevaporated to dryness
  7. customto afford a brown oil, 1.57 g, 95%

Sources & evidence

ORD record
ord-118a02af6f9845999a1c7ea124b84fdc
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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