Diethyl Ether → Methyl 5-(2-bromoacetyl)-2-(phenylmethoxy)benzoate

HRID 724580Notes

Reaction equation

HRID 724580 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br:22]Br.C(OCC)C>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH2:11][Br:22])[CH:7]=[CH:6][C:5]=1[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 12368981Benzoic acid, 5-acetyl-2-(phenylmethoxy)-, methyl ester

Product 1

HCID 11824614Methyl 5-(2-bromoacetyl)-2-(phenylmethoxy)benzoateYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent2×

Procedure

The product of step (a) (10.0 g, 35.2 mmol) was dissolved in chloroform (250 mL) in a 500 mL flask under a nitrogen atmosphere. Bromine (1.63 mL, 31.7 mmol) dissolved in chloroform (50 mL) was added using a dropping funnel over 30 min. The reaction mixture was stirred for 2.5 h and then concentrated to give a solid. The solid was dissolved in toluene (150 mL) with some gentle heat, followed by the addition of ethyl ether (150 mL) to yield the title compound as a crystalline solid (55% yield).

Workup

  1. additionwas added
  2. customover 30 min
  3. concentrationconcentrated
  4. customto give a solid

Sources & evidence

ORD record
ord-0b6b92d9676f469d963d11e81d1d5fa1
Source dataset
uspto-grants-2006_11
Patent number
US07141671B2

Reaction notes

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