Synthesis of 3-bromo-1,1-diphenylacetone

Preparation of 3-bromo-1,1-diphenylacetone

Preparation of 3-bromo-1,1-diphenylacetone

Preparation of 3-bromo-1,1-diphenylacetone

A solution of diphenylacetyl chloride (0.057 mole) in dry ether (100 ml) is dropped into a stirred, ice-cold ethereal solution of diazomethane (from 20 g of methylnitrosourea). The mixture is left for 30 min at 0° C and then for 1 hours at room temperature, after which the excess of diazomethane and the ether are distilled off and the residue is dissolved in dry ether (100 ml). Into this solution is dropped a mixture of 48 % hydrobromic acid (14 ml) and ether (14 ml), if desired with ice-cooling. When the evolution of nitrogen stops, the solution is concentrated. The 3-bromo-1,1-diphenylacetone crystallizes and, when recrystallized from methanol or 2-propanol, has m.p. 66-67°.

J. Org. Chem., 12, 769 (1947).

J. Amer. Chem. Soc, 74, 2083 (1952).

IUPAC Name

3-bromo-1,1-diphenylpropan-2-one

InChI

InChI=1S/C15H13BrO/c16-11-14(17)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2

InChI Key

MXUDDMSHZFPMLF-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(C2=CC=CC=C2)C(=O)CBr

Depositor-Supplied Synonyms

3-bromo-1,1-diphenylacetone, 33609-25-5, 3-bromo-1,1-diphenylpropan-2-one, ZINC00161973, zlchem 852, AC1MDRJQ, SCHEMBL6335418, CTK4H0957, DTXSID60383280, ZLD0313, MXUDDMSHZFPMLF-UHFFFAOYSA-N, ZINC161973, 1-bromo-3,3-diphenyl-2-propanone, ACT06188, 3-Bromo-1,1-diphenyl-2-propanone, 1,1-diphenyl-3-bromo-propan-2-one, MFCD03822127, 2-Propanone,3-bromo-1,1-diphenyl-, AKOS022507551, MO00869, AK391965, OR064544, FT-0615121, I14-100878

Removed Synonyms

CID2794635

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