Carbon tetrabromide → 2-(Bromomethyl)-3-chloro-1-benzothiophene

HRID 604625

반응식

HRID 604625 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[Cl:25][C:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[S:28][C:27]=1CO>C(Cl)Cl>[Br:24][CH2:20][C:27]1[S:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:26]=1[Cl:25]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 821965(3-Chloro-1-benzothien-2-yl)methanol

생성물 1

HCID 8167082-(Bromomethyl)-3-chloro-1-benzothiophene

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of triphenylphosphine (1.74 g, 6.62 mmol) in dry CH2Cl2 (6 mL) was added dropwise to a stirred solution of carbon tetrabromide (2.20 g, 6.62 mmol) and (3-chloro-1-benzothien-2-yl)methanol (0.94 g, 4.73 mmol) in dry CH2Cl2 (35 mL) at 0° C. under N2. The reaction was allowed to warm to room temperature and was stirred for 4 h then concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 40×160 nm, 0-25% EtOAc in hexanes gradient) to afford 2-(bromomethyl)-3-chloro-1-benzothiophene. Rf=0.93 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3): δ 7.81 (dd, J=1.3, 7-1 Hz, 1H); 7.78 (dd, J=1.2, 7.2 Hz, 1H); 7.47-7.41 (m, 2H); 4.81 (s, 2H).

후처리

  1. concentrationthen concentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by flash chromatography (Si, 40×160 nm, 0-25% EtOAc in hexanes gradient)

출처 및 근거

ORD 기록
ord-b34e4a9d8d7b4538832fea2ce15af53d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

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