Formic Acid → 2-Fluoro-5-(hydroxymethyl)benzonitrile

HRID 1386049노트

반응식

HRID 1386049 반응식
[CH:1]([OH:3])=O.C(N(CC)CC)C.[C:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[F:21])CBr)#[N:12].Cl>C(#N)C.CO.O>[C:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:1][OH:3])#[N:12]

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27739315-(Bromomethyl)-2-fluorobenzonitrile

생성물 1

HCID 27739342-Fluoro-5-(hydroxymethyl)benzonitrile

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 22242641Methanol--water (1/1)용매

실험 절차

A solution of 85% formic acid (0.63 mL) and triethylamine (2.32 mL, 16.7 mmol) in acetonitrile at 0° C. was treated with the product from Example 82A (1.3 g, 5.6 mmol), stirred at room temperature for 3 hours, the reaction evaporated to dryness, partitioned between ethyl acetate/water, the organic layer dried with sodium sulfate, filtered and solvent evaporated to provide a crude formate ester. This residue was dissolved in methanol:water (5:1), treated with a catalytic amount of concentrated hydrochloric acid, stirred at room temperature overnight, evaporated to dryness, and flash chromatographed over silica gel eluting with ethyl acetate:hexane (1:1) to provide 0.40 g 3-cyano-4-fluorobenzyl alcohol.

후처리

  1. customthe reaction evaporated to dryness
  2. custompartitioned between ethyl acetate/water
  3. dry with materialthe organic layer dried with sodium sulfate
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customto provide a crude formate ester
  7. stirringstirred at room temperature overnight
  8. customevaporated to dryness, and flash
  9. customchromatographed over silica gel eluting with ethyl acetate:hexane (1:1)

출처 및 근거

ORD 기록
ord-70f73e46840f42318450eab35c65ac06
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265417B1

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