Benzyl Bromide → HCID 58248139, compound

HRID 1496825Notes

Reaction equation

HRID 1496825 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH2:22]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:4]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58248137HCID 58248137, compound

Product 1

HCID 58248139HCID 58248139, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ester 9 (4.9 g, 18.0 mmol) in anhydrous DMF (20 mL) was added potassium carbonate (5 g, 36.0 mmol) and benzyl bromide (3.38 g, 19.8 mmol). The reaction mixture was stirred overnight at room temperature, filtered and the solvent was removed under reduced pressure. The resulting crude reaction product was suspended in water and extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered, and the volatiles were removed in vacuo to give 6.06 g of bromoaryl 10 as a white solid. Yield 93%. 1H NMR (300 MHz, CDCl3) δ ppm: 7.94 (d, J=15.9 Hz, 1H), 7.42 (d, J=8.7 Hz, 1H), 7.38-7.25 (m, 5H), 7.14 (d, J=3.0 Hz, 1H), 6.81 (dd, J1=9.0 Hz, J2=3.0 Hz, 1H), 6.29 (d, J=15.9 Hz, 1H), 5.00 (s, 2H), 4.23 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm: 166.2, 158.0, 142.8, 136.1, 135.1, 133.9, 128.6, 128.2, 127.4, 121.1, 118.3, 116.1, 113.6, 70.2, 60.6, 14.2; HRMS (EI) m/z: calcd for C18H17BrO3: 360.0361. found: 360.0361; mp: 72-74° C.

Workup

  1. filtrationfiltered
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting crude reaction product
  4. extractionextracted with AcOEt
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-deca141595564c30b785536099b3e295
Source dataset
uspto-grants-2015_12
Patent number
US09199936B2

Reaction notes

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