Benzyl Bromide → HCID 18006245, compound

HRID 1259029Notes

Reaction equation

HRID 1259029 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7]Br)=[CH:3][CH:2]=1.[OH:9][C:10]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C([O-])(O)=O.[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:9][C:10]1[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:16]=[CH:15][C:11]=1[C:12]([O:14][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 1645782-Hydroxy-4-(trifluoromethyl)benzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 18006245HCID 18006245, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

BnBr (1.20 mL, 8.325 mmol) was added to a solution of 2-hydroxy-4-(trifluoromethyl)benzoic acid (1.50 g, 7.277 mmol) in TBAF (10 mL, 1 M solution in THF) and the mixture was stirred at r.t. for 2 h. The reaction mixture was poured into NaHCO3 (saturated aqueous solution, 100 mL) and extracted with EtOAc (100 mL). It was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (5→30% EtOAc/hexanes) to furnish 2.18 g of benzyl 2-hydroxy-4-(trifluoromethyl)benzoate (colourless oil, yield: quantitative).

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. dry with materialIt was dried over Na2SO4 (anhydrous)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on SiO2 (5→30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-22f2be82c73449dfab18b49092242fdd
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

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