Water → HCID 28878728, compound

HRID 2264813Notes

Reaction equation

HRID 2264813 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.O>ClCCCl>[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108934-IodoanilineHCID 67970o-FluorobenzaldehydeHCID 2724942Triacetoxyborohydride

Product 1

HCID 28878728HCID 28878728, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-iodoaniline (1 g, 4.5 mmol), 2-fluorobenzaldehyde (0.48 ml, 0.566 g, 4.5 mmol) and triacetoxyborohydride (1.9 g, 9.0 mmol) in 1,2-dichloroethane (20 ml) was stirred for 4 days at room temperature. After addition of water the mixture was extracted with DCM. The combined organic layers were dried (Na2SO4), filtered and evaporated to give the title compound (1.612 g, quant.). The crude material was used without further purification. MS: (ES/+) m/z: 328 [MH+], C13H11FIN requires 327; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.4-7.1 (m, 6H), 6.4 (d, 2H), 4.3 (m, 1H), 2.5 (m, 2H).

Workup

  1. extractionwas extracted with DCM
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-2654683b5e1c4adeaec743654aeda470
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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