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

HRID 41387Notes

Reaction equation

[CH3:1][C:2]([CH3:4])=O.[Br:5][C:6]1[C:7]([OH:16])=[CH:8][C:9]([OH:15])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH2:1]([O:12][C:11](=[O:13])[C:10]1[CH:14]=[C:6]([Br:5])[C:7]([O:16][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[O:15][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:2]1[CH:4]=[CH:10][CH:14]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a 10 L jacketed vessel, fitted with a flange lid containing stirrer, thermometer and dropping funnel, was charged acetone (2.5 L) followed by 5-bromo-2,4-dihydroxybenzoic acid (100 g, 0.43 mol) and potassium carbonate (356 g, 2.58 mol). To the stirring mixture at ambient was added benzyl bromide (185 mL, 1.55 mol) at a rate of ˜20 ml/min. The mixture was heated at 60° C. for 18 h and then taken to 45° C. Water (1.5 L) was added and the mixture stirred for 30 min. The mixture was extracted with EtOAc (2×1 L) and the combined organic portions reduced in vacuo. To the residue was added Et2O (200 mL) and petroleum ether (1 L), the mixture stirred for 30 min and the solid formed collected by filtration and dried in vacuo to give the title compound (197.2 g) as a white solid.

Workup

customfitted with a flange lid
additioncontaining stirrer
customtaken to 45° C
extractionThe mixture was extracted with EtOAc (2×1 L)
additionTo the residue was added Et2O (200 mL) and petroleum ether (1 L)
stirringthe mixture stirred for 30 min
customthe solid formed
filtrationcollected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-b41116e7852a494bb2ea26c72ba2b7ce
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530469B2

Reaction notes

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