Benzyl Alcohol → HCID 21544502, compound

HRID 576592Notes

Reaction equation

[H-].[Na+].C1COCC1.[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.F[C:17]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:18]=1[C:19]#[N:20]>CCOC(C)=O>[CH2:8]([O:15][C:17]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][C:18]=1[C:19]#[N:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Intermediate B, Step 1: A 250-mL round bottom flask containing a magnetic stir bar and fitted with a condenser and a inert gas inlet was charged successively with sodium hydride (60% dispersion in mineral oil, 1.32 g, 33.0 mmol), THF (46 mL) and a THF (46 mL) solution of benzyl alcohol (2.86 mL, 27.5 mmol) and 2-fluoro-5-(trifluoromethyl)benzonitrile (5.2 g, 27.5 mmol). The resulting solution was warmed to 60° C. for 3 h, then cooled to RT, diluted with EtOAc (200 mL) and washed with water (2×100 mL) and brine (60 mL). The organic layer was dried (MgSO4) and concentrated on a rotary evaporator to give crude 2-(benzyloxy)-5-(trifluoromethyl)benzonitrile (7.32 g, 26.4 mmol, 96% yield) as a colorless oil. LC/MS [M+H]+=278.07. 1H-NMR (400 MHz, CDCl3) δ=7.89 (s, 1H), 7.78 (d, J=12.0 Hz, 1H), 7.5-7.3 (m, 5H), 7.12 (d, J=8.0 Hz, 1H), 5.31 (s, 2H).

Workup

customfitted with a condenser and a inert gas inlet
temperaturecooled to RT
washwashed with water (2×100 mL) and brine (60 mL)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-4ede56d30ed845d9bf53c5f699835f9e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040526B2

Reaction notes

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