Water → (6-Methyl-[1,1'-biphenyl]-3-yl)methanol

HRID 270005

반응식

HRID 270005 반응식
I[C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:7]1[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][C:4]([CH2:9][OH:10])=[CH:5][CH:6]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 51667983-Iodo-4-methylbenzyl alcohol

생성물 1

HCID 23089113(6-Methyl-[1,1'-biphenyl]-3-yl)methanol수율 88.2%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

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온도
100 °C

실험 절차

To a mixture of compound PPP, (3-iodo-4-methyl-phenyl)-methanol, (4 g, 16.12 mmol) and phenylboronic acid (2.06 g, 16.89 mmol) in 1-propanol (30 mL) was successively added palladium(II) acetate (0.01276 g, 0.05 mmol), triphenyl phosphine (0.042 g, 0.161 mmol), aq. sodium carbonate solution (2 M, 11.44 mL, 22.88 mmol), and water (6 mL). The mixture was heated to 100° C. until reaction is complete (tlc), cooled, quenched with water (20 mL) and extracted into ethyl acetate (3×50 mL). Combined organic layer was washed with 2% aq. sodium bicarbonate (2×25 mL), brine (1×50 mL), dried (MgSO4) and concentrated to yield 2.82 g of (6-methyl-biphenyl-3-yl)-methanol, compound QQQ, that was directly taken into next step without any further purification; Rt: 10.95 min.

후처리

  1. temperaturecooled
  2. customquenched with water (20 mL)
  3. extractionextracted into ethyl acetate (3×50 mL)
  4. washCombined organic layer was washed with 2% aq. sodium bicarbonate (2×25 mL), brine (1×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-317df5cd4eb34632a371a9c245d9c4e2
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449481B2

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