Synthesis of 1-bromo-2-chlorobenzene

Preparation of 1-bromo-2-chlorobenzene

Preparation of 1-bromo-2-chlorobenzene

Preparation of 1-bromo-2-chlorobenzene

A solution of sodium nitrite (1 mole) in water (125 ml) is added, rapidly, with stirring and cooling in ice, to a mixture of o-chloroaniline (1 mole) and 48 % hydrogen bromide (300 ml, 2.5 moles) at 0°C; small pieces of ice are also added so as to maintain the temperature below 10°C. The solution be kept distinctly acid to Congo Blue during the diazotization. The last few ml of sodium nitrite solution are added slowly, being stopped when the solution changes starch-iodide paper to blue. In a flask fitted with a descending condenser, dropping funnel, and steam-inlet (at first shut off) copper(I) bromide (0.55 mole) and 48% hydrogen bromide (80 ml) are heated to the boiling point. Then, whilst heating is maintained, the diazonium salt solution (removed in portions from the cold bath) is run in during about 30 min, during which a large part of the 0-bromochlorobenzene distills. After this addition a powerful stream of steam is blown through the solution until 1-1.5 liter of distillate has been collected. The organic layer is separated and washed successively with concentrated sulfuric acid (ca. 4 x 10 ml; until the acid is only weakly colored), water, 5 % sodium hydroxide solution, and water, dried over calcium chloride (3 g), and distilled. The product (89-95% yield) has b.p. 199-201°C/742 mm.

Org. Syn., 24, 22 (1944); Coll. Vol. Ill, 185 (1955).

IUPAC Name

1-bromo-2-chlorobenzene

InChI

InChI=1S/C6H4BrCl/c7-5-3-1-2-4-6(5)8/h1-4H

InChI Key

QBELEDRHMPMKHP-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C(=C1)Cl)Br

Depositor-Supplied Synonyms

1-Bromo-2-chlorobenzene, 2-BROMOCHLOROBENZENE, 694-80-4, 2-Chlorobromobenzene, o-Bromochlorobenzene, o-Chlorobromobenzene, Benzene, 1-bromo-2-chloro-, Bromochlorobenzene, 2-Bromo-1-chlorobenzene, 1-Chloro-2-bromobenzene, 1-bromo-2-chloro-benzene, 2-Bromochluorobenzene, Benzene, bromochloro-, MFCD00000532, OTAVA-BB 1287417, QBELEDRHMPMKHP-UHFFFAOYSA-N, 28906-38-9, ST50406321, 2-bromoclorobenzene, 2-chloro-bromobenzene, PubChem3582, AC1Q3HEN, AC1Q3HEO, UNII-PEC7Z3YX6P, ACMC-1BCK9, PEC7Z3YX6P, AC1L20AD, B60401_ALDRICH, KSC203E7J, SCHEMBL251393, 1-bromanyl-2-chloranyl-benzene, 442333_SUPELCO, TPC-I131, CTK1A3274, ZINC404308, NSC59694, STR07176, EINECS 211-775-1, EINECS 249-303-1, ANW-35692, NSC 59694, NSC-59694, ZINC00404308, AKOS005265527, AS03126, CS21391, RP25113, TRA0093667, AJ-22316, AK-47441, AN-47249, BC002489, BR-47441, KB-21690, OR011410, OR145047, OR253355, R716, SC-65924, ZB013461, AB0007254, AI3-31290, DB-020717, KB-204385, ST2408690, TL8004873, TR-023115, A9191, AM20050050, B0569, EN300-31033, M-6298, 46622-EP2311826A2, A836511, I01-0599, T7082629, W-104621, InChI=1/C6H4BrCl/c7-5-3-1-2-4-6(5)8/h1-4, UNII-Z0W07Y466G component QBELEDRHMPMKHP-UHFFFAOYSA-N

Removed Synonyms

C6H4BrCl, MolPort-000-151-788, CID12754, RTR-023115

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