Boron tribromide → HCID 58934952, compound

HRID 855017Notes

Reaction equation

HRID 855017 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13]C)[O:9][CH:8]([C:15]([F:18])([F:17])[F:16])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6]2)[CH3:2].B(Br)(Br)Br>C(Cl)Cl.C(=O)=O.CC(C)=O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][CH:8]([C:15]([F:16])([F:17])[F:18])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6]2)[CH3:2]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 69518051HCID 69518051, compound

Product 1

HCID 58934952HCID 58934952, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18522661Acetone cardiceSolvent

Procedure

To a solution of 6.8 g (20.6 mmol) of ethyl 6-ethyl-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 30 mL of anhydrous DCM at −78° C. in dry ice/acetone bath was added dropwise a solution of 206 ml (1.0 M in DCM, 206 mmol) of boron tribromide. After finishing addition, the dry ice/acetone bath was removed. The reaction was stirred at room temperature overnight. The reaction was cooled back to −78° C. in dry ice/acetone bath and treated dropwise with 250 mL of methanol. The reaction was allowed to warm to room temperature and subsequently concd in vacuo. The residue was purified by silica chromatography with EtOAc/hexane (2:8). The collected fractions were concd and used directly in step 3.

Workup

  1. additionaddition
  2. customthe dry ice/acetone bath was removed
  3. temperatureThe reaction was cooled back to −78° C. in dry ice/acetone bath
  4. additiontreated dropwise with 250 mL of methanol
  5. temperatureto warm to room temperature
  6. customThe residue was purified by silica chromatography with EtOAc/hexane (2:8)

Sources & evidence

ORD record
ord-9a27c31eacec437586966709332ee96f
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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