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

HRID 82779

反応式

HRID 82779 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 219768984-(Benzyloxy)-3-fluorobenzaldehyde収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-3841b984b0134e28bf554ba3eafab8b1
出典データセット
uspto-grants-2014_09
特許番号
US08846737B2

関連ノート

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