Synthesis of 4-bromoacetanilide (p-bromoacetanilide; N-(4-bromophenyl)acetamide)

Preparation of 4-bromoacetanilide

Preparation of 4-bromoacetanilide (p-bromoacetanilide; N-(4-bromophenyl)acetamide)

Preparation of 4-bromoacetanilide (p-bromoacetanilide; N-(4-bromophenyl)acetamide)

1 g of finely powdered acetanilide is dissolved in 5 ml of cold glacial acetic acid. To this solution 0.42 ml (or 1.34 g) of bromine dissolved in 6 ml of glacial acetic acid is added. The mixture is vigorously shaken and left for 15 minutes to stand at room temperature. The reddish-orange solution of 4-bromoacetanilide is poured in large excess cold water. 4-Bromoacetanilide is separated by filtration, the crystals are washed with water and finally recrystallized from ethanol. The 4-bromoacetanilide is obtained as colourless crystals, which melt at 167° C. The yield of final product is around 1 g.

Practical organic chemistry, by F. G. Mann, 166-167, 1960

IUPAC Name

N-(4-bromophenyl)acetamide

InChI

InChI=1S/C8H8BrNO/c1-6(11)10-8-4-2-7(9)3-5-8/h2-5H,1H3,(H,10,11)

InChI Key

MSLICLMCQYQNPK-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC1=CC=C(C=C1)Br

Depositor-Supplied Synonyms

4′-Bromoacetanilide, p-Bromoacetanilide, N-(4-Bromophenyl)acetamide, 4-BROMOACETANILIDE, 103-88-8, Bromoanilide, Bromoantifebrin, Antisepsin, Asepsin, N-Acetyl-4-bromoaniline, Acetamide, N-(4-bromophenyl)-, Acetanilide, 4′-bromo-, 1-Bromo-4-acetamidobenzene, p-Bromo-N-acetanilide, Acetanilide, p-bromo-, USAF DO-40, N-(4-Bromo-phenyl)-acetamide, N-Acetyl-p-bromoaniline, NSC 105442, MSLICLMCQYQNPK-UHFFFAOYSA-N, EINECS 203-154-9, SBB054161, BRN 2208091, AI3-01799, WLN: ER DMV1, F1962-0210, Bromoanalide, p-Bromoacetanalide, 4′-bromoacetoanilide, C8H8BrNO, AC1L1PBF, Maybridge4_002362, N-(p-Bromophenyl)acetamide, AC1Q1KP4, AC1Q1KP5, SCHEMBL9674, ACMC-1C80Z, NCIOpen2_007075, N-(4-bromophenyl)-acetamide, CHEMBL59019, UNII-4KB44F25A3, Acetamide,N-(4-bromophenyl)-, 161659_ALDRICH, Acetamide, N-(p-bromophenyl)-, Jsp000395, CTK4A2484, NSC8048, MolPort-000-150-450, 4KB44F25A3, HMS1527L08, 1-(N-Acetylamino)-4-bromobenzene, ACT03706, NSC-8048, STR01944, ANW-14991, NSC105442, STL089501, ZINC00149704, AKOS000201828, AS00912, MCULE-6298046548, NE10003, NSC-105442, NCGC00176635-01, AC-18809, AN-24660, FS003009, H248, KB-37333, LS-10491, SC-26629, TL806151, TS-03575, ZB005051, KB-107361, KB-259202, B0534, FT-0617847, ST50308642, EN300-15537, AG-205/03191041, I01-7154, BRD-K54936524-001-01-0, 3B3-011418

Removed Synonyms

Bromoacetanilide, monobromoacetanilide, (4-BROMOPHENYL)ACETAMIDE, CID7683, A1887, 4-12-00-01504 (Beilstein Handbook Reference)

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