Synthesis of 4-bromoanisole

Preparation of 4-bromoanisole

Preparation of 4-bromoanisole by bromination anisole with bromine

Preparation of 4-bromoanisole

Preparation of 4-bromoanisole

To the round bottom flask equipped with a dropping funnel and reflux condenser 22 g (0.2 mol) of anisole were placed. The flask was heated to a gentle boiling and slowly from a dropping funnel 32 g (0.2 mol) of bromine were added at a such rate that, after addition of one drop of bromine the color disappeared after a few seconds (the disappearance of the bromine color occurs in the gas phase above the boiling liquid). After adding all bromine mixture was heated for a further 15 minutes, then cooled and added 100 ml of ether. The ether solution was transferred to a separatory funnel, washed with dilute sodium hydroxide solution, then with water, dried over anhydrous calcium chloride and filtered. The ether was removed, and the residue is distilled, taking a fraction boiling at 213-223° C. Yield about 23 g (or 60% of the theoretical). 4-bromoanisole, heavy liquid with a characteristic odor. The boiling point may differ depending on the synthesis procedure used fort he preparation 4-bromoanisole  (213-216 ° C or 223 ° C); 4-bromoanisole obtained as described above boils at 215-216 °, melting point 11.5 °, nD=1.5605.

4-Bromoanisole are obtained by bromination with bromine in a solution of anisole in solution of carbon disulfide, acetic acid or chlorofor. Bromination is also performed with phosphorus pentabromide.

Препаративная органическая химия, Вульфсон Н.С., 195, 1959 (Preparative organic chemistry, Wolfson N. S., 195, 1959)

IUPAC Name

1-bromo-4-methoxybenzene

InChI

InChI=1S/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3

InChI Key

QJPJQTDYNZXKQF-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=C(C=C1)Br

Depositor-Supplied Synonyms

4-BROMOANISOLE, 1-Bromo-4-methoxybenzene, 104-92-7, p-Bromoanisole, Benzene, 1-bromo-4-methoxy-, 4-Methoxybromobenzene, Anisyl bromide, p-Anisyl bromide, Anisole, p-bromo-, p-Bromanisole, p-Methoxyphenyl bromide, 4-Methoxyphenyl bromide, p-Bromophenyl methyl ether, p-Methoxybromobenzene, 4-Methoxy-1-bromobenzene, 4-Bromoanisol, 4-bromo anisole, 1-bromo-4-methoxy-benzene, 4-BROMO ANISOL, NSC 8042, 4-bromo-1-methoxybenzene, BROMOANISOLE(4-), QJPJQTDYNZXKQF-UHFFFAOYSA-N, EINECS 203-252-1, SBB060208, AI3-01295, PARAGOS 530458, OTAVA-BB 1287415, LABOTEST-BB LTBB001561, 4bromoanisole, p-bromoanisol, p-bromo anisole, p-bromo-anisole, para-bromoanisole, parabromo-anisole, 4-bromo-anisole, 4-anisyl bromide, p-Bromomethoxybenzene, 4-bromomethoxybenzene, PubChem3726, 4-methoxy-bromobenzene, ACMC-1BPJE, 4-bromophenyl methyl ether, 1-bromo-4-methoxy benzene, AC1L1PF6, AC1Q49HF, SCHEMBL9301, B56501_ALDRICH, 1-bromanyl-4-methoxy-benzene, KSC177G3P, UNII-U430F901J9, CHEBI:47257, CTK0H7337, NSC8042, MolPort-001-768-360, ACT04984, NSC-8042, STR04213, ANW-15145, BR1023, ZINC00404306, AKOS000119001, AS02358, AS04200, PS-5119, RP24698, RTC-060531, TF10501, U430F901J9, AJ-22314, AK-59802, AN-24697, BC676620, BR-59802, CJ-03999, KB-37335, LS-20206, SC-00205, KB-240439, ST2408729, TC-060531, TL8000193, AM20020130, B0547, FT-0081674, FT-0612055, FT-0617854, ST50406339, A801100, I01-0457, InChI=1/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H

Removed Synonyms

bromoanisole, CID7730, BOP

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