Benzyl Bromide → Benzyl-2,4-bis-benzyloxy-5-bromobenzoate

HRID 2079847Notes

Reaction equation

HRID 2079847 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([OH:11])[C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:19]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Br:12])[C:9]([O:11][CH2:19][C:16]2[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=2)=[CH:10][C:2]=1[O:1][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1)[C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 818145-Bromo-2,4-dihydroxybenzoic acid

Product 1

HCID 46915635Benzyl-2,4-bis-benzyloxy-5-bromobenzoateYield 189.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 2,4-dihydroxy-5-bromobenzoic acid (23.3 g, 0.1 mol), BnBr (54 g, 0.33 mol) and excess K2CO3 (80 g, 0.58 mol) was stirred in acetone (500 ml) at 85° C. overnight. HPLC indicated the completion of the reaction. After cooling to r.t, the reaction was filtered, and the filtrate was concentrated to give 2,4-bis-benzyloxy-5-bromo-benzoic acid benzyl ester as a white solid (47.8 g, 95%). M.p.: 74-76° C.; 400 MHz 1H NMR (CDCl3) δ: 8.13 (s, 1H), 7.41-7.28 (m, 15H), 6.53 (s, 1H), 5.32 (s, 2H); 5.12 (s, 2H), 5.08 (s, 2H); LCMS: 503, 505 [M+H].

Workup

  1. customthe completion of the reaction
  2. temperatureAfter cooling
  3. filtrationthe reaction was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b42e1259f98149898be3e74400911f5a
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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