Methanol → Methyl 2-(4-bromophenyl)-2-phenylacetate

HRID 1525242Notes

Reaction equation

HRID 1525242 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:23]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]([O:11][CH3:23])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 38473074-Bromo-alpha-phenylbenzeneacetic acid2×

Product 1

HCID 57779541Methyl 2-(4-bromophenyl)-2-phenylacetate

Conditions

Temperature
60 °C

Procedure

To a solution of compound 2-(4-Bromophenyl)-2-phenylacetic acid, 14-c, (5.6 g, 19.3 mmol) in methanol (200 mL) was added concentrated sulfuric acid (6 mL) and the reaction mixture was stirred at 60° C. for 14 h. The resulting solution was concentrated and ice-water was added. The aqueous layer was extracted by EA. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to yield title compound, 14-d, (5.5 g, 93%). 1H NMR (300 MHz, CDCl3) δ3.73 (s, 3H), 4.96 (s, 1H), 7.16 (d, J=8.4 Hz, 2H), 7.25-7.30 (m, 5H), 7.42 (d, J=8.4 Hz, 2H). LC-MS: (M+H)+ 304, 306.

Workup

  1. concentrationThe resulting solution was concentrated
  2. additionice-water was added
  3. extractionThe aqueous layer was extracted by EA
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c4e1586afa84b1d82e002af4d908758
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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