Benzyl Bromide → 4-(Benzyloxy)-3-fluorobenzaldehyde

HRID 82779

반응식

HRID 82779 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[CH2:11]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[F:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5872503-Fluoro-4-hydroxybenzaldehyde

생성물 1

HCID 219768984-(Benzyloxy)-3-fluorobenzaldehyde수율 81%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-fluoro-4-hydroxybenzaldehyde (4.264 g, 30.0 mmol), benzyl bromide (5.986 g, 35.0 mmol, 4.16 mL) and K2CO3 (820 g, 59.0 mmol) in DMF (50 mL) was stirred for 48 hours at room temperature before EtOAc (100 mL) and water (50 mL) were added. The organic layer was separated, washed with water (2×50 mL), brine (30 mL) and dried (Na2SO4). Concentration in vacuo gave a white solid residue. Recrystallization from CH2Cl2/n-hexane afforded CAB06038 as colorless needles (5.59 g, 81%). Mp. 94-95° C.; 1H NMR (400 MHz, CDCl3) δ 524 (s, 2H), 7.12 (dd, J=8.2, 8.2 Hz, 1H), 734-7.48 (m, 5H), 7.59-7.66 (m, 2H), 9.85 (d, J=2.0 Hz, 1H); LRMS (ES+): m/z 231.1 (100%, [M+H]+).

후처리

  1. additionwere added
  2. customThe organic layer was separated
  3. washwashed with water (2×50 mL), brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationConcentration in vacuo
  6. customgave a white solid residue
  7. customRecrystallization from CH2Cl2/n-hexane

출처 및 근거

ORD 기록
ord-3841b984b0134e28bf554ba3eafab8b1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846737B2

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