Carbon tetrabromide → 1-[2-(Benzyloxy)ethoxy]-4-(bromomethyl)-2-tert-butoxybenzene

HRID 591324Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][C:13]=1[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][Br:25])=[CH:14][C:13]=1[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 0.9 g (2.2 mmol) {4-[2-(benzyloxy)ethoxy]-3-tert-butoxyphenyl}methanol and 976 mg (2.94 mmol) tetrabromo methane in 9 ml THF was added 775 mg (2.96 mmol) triphenylphosphin diluted in 4.5 ml THF at 0° C. dropwisly. The reaction mixture was stirred for 1 h at 0° C. The suspension was filtrated. The filter cake was washed with THF. The combined filtrates were concentrated in vacua. The crude product is purified by column chromatography (silica gel, hexane/ethylacetate gradient: 99:1→1:99). The desired product was obtained in 28% yield (313 mg, 0.76 mmol).

Workup

filtrationThe suspension was filtrated
washThe filter cake was washed with THF
concentrationThe combined filtrates were concentrated in vacua
customThe crude product is purified by column chromatography (silica gel, hexane/ethylacetate gradient: 99:1→1:99)

Sources & evidence

ORD record: ord-04c68cfb87ae4f7b9e47ccce7ad4e690
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238631B2

Reaction notes

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