Benzyl Bromide → HCID 67144534, compound

HRID 1968607Notes

Reaction equation

HRID 1968607 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.CCOCC>[CH2:13]([O:12][C:4]1[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 67144534HCID 67144534, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 4-fluoro-2-hydroxybenzoate (2.00 g), benzyl bromide (1.54 mL), and cesium carbonate (4.60 g) in N,N-dimethylformamide (50 mL) were stirred in for 24 hours. The reaction was taken up in ether and washed 3× with 1M NaOH solution and with brine, then concentrated to give the title compound.

Workup

  1. washwashed 3× with 1M NaOH solution
  2. concentrationwith brine, then concentrated

Sources & evidence

ORD record
ord-5adec329bfb449b5adf39f4385ee11a0
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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