Carbon tetrabromide → 2-Bromomethyl-3-(2-trimethylsilylethoxymethoxy)-naphthalene

HRID 1004947Notes

Reaction equation

[CH3:1][Si:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[C:9]([CH2:18]O)=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2.C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Br:23][CH2:18][C:9]1[C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:21])([CH3:20])[CH3:1])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

400 mg (1.30 mmol) of [3-(2-trimethylsilylethoxy-methoxy)-naphthalen-2-yl]-methanol and 462 mg (1.81 mmol) of carbon tetrabromide were dissolved in 5 ml of absolute acetonitrile and the solution was cooled to 0° C. A solution of 446 mg (1.68 mmol) of triphenylphosphine in 6 ml of absolute acetonitrile was added dropwise thereto at 0° C. within 10 minutes and thereafter the mixture was stirred at 0° C. for a further 30 minutes. Subsequently, the solvent was distilled off under reduced pressure and, for purification, the crude product was chromatographed, without further working up, on silica gel using a 2:3 mixture of methylene chloride and hexane as the eluent. There were obtained 314 mg (65% of theory) of 2-bromomethyl-3-(2-trimethylsilylethoxymethoxy)-naphthalene as a light yellow oil; MS: 366, 368 (M)+.

Workup

distillationSubsequently, the solvent was distilled off under reduced pressure and, for purification
customthe crude product was chromatographed
additiona 2:3 mixture of methylene chloride and hexane as the eluent

Sources & evidence

ORD record: ord-81b67d23a422419690af1bbf686027cc
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06051712

Reaction notes

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