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

HRID 591324
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HRID 591324 반응식
[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
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참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 70978543{4-[2-(Benzyloxy)ethoxy]-3-tert-butoxyphenyl}methanol

생성물 1

HCID 1177786181-[2-(Benzyloxy)ethoxy]-4-(bromomethyl)-2-tert-butoxybenzene수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-04c68cfb87ae4f7b9e47ccce7ad4e690
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238631B2

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