Dichloromethane → HCID 58934553, compound

HRID 855030Notes

Reaction equation

HRID 855030 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10]C=1)[O:8][CH:7]([C:12]([F:15])([F:14])[F:13])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]2.I[Cl:22].C(OCC)(=O)C.Cl[CH2:30][Cl:31]>>[Cl:22][C:3]1[C:2]([OH:1])=[C:30]([Cl:31])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]([C:12]([F:15])([F:14])[F:13])[O:8]2

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 8857Ethyl AcetateHCID 24640Iodine chlorideHCID 58934503HCID 58934503, compound

Product 1

HCID 58934553HCID 58934553, compoundYield 64%

Procedure

To a solution of 1.0 g (3.5 mmol) of ethyl 6-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 10 mL of anhydrous dichloromethane was added a solution of 1.5 mL (30 mmol) of iodomonochloride in 5 mL anhydrous dichloromethane. The resulting brown solution was stirred at room temperature for one hour. The reaction was added to 50 mL of ethyl acetate. The organic solution was washed with sat. sodium sulfite solution three times, washed with brine three times and dried over anhydrous magnesium sulfate. Concentration in vacuo afforded 0.8 g (64%) of a yellow solid: 1H NMR (CDC3/300 MHz) 8.00 (s, 1H), 7.01(s, 1H), 5.81(s, 1H), 5.70(q, J=6.6 Hz, 1H), 4.38(m, 2H), 1.40(t, J=7.2 Hz, 3H); MS (ESI+) 357.0 (M+1, 100).

Workup

  1. washThe organic solution was washed with sat. sodium sulfite solution three times
  2. washwashed with brine three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-f2b04738577f43b0b65f6b49594fa292
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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