Carbon tetrabromide → HCID 18620081, compound

HRID 1862614Notes

Reaction equation

HRID 1862614 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([C:17]([F:20])([F:19])[F:18])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:41].C(=O)(O)[O-].[Na+]>ClCCl>[Br:41][CH2:2][CH2:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([C:17]([F:20])([F:19])[F:18])[CH:5]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 18620096HCID 18620096, compound

Product 1

HCID 18620081HCID 18620081, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-[4-(2-hydroxyethyl)-2-(trifluoromethyl)phenoxy]acetate (224 mg) in dichloromethane (2 ml) were added triphenylphosphine (260 mg) and carbon tetrabromide (396 mg), and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into a saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The extract was washed with water and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent:dichloro-methane/hexane=1/1) gave ethyl 2-[4-(2-bromoethyl)-2-(trifluoromethyl)phenoxy]acetate (178 mg).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent:dichloro-methane/hexane=1/1)

Sources & evidence

ORD record
ord-7c50097e1fa240b7bd02461738526c46
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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