Water → HCID 11312729, compound

HRID 2100174Notes

Reaction equation

HRID 2100174 reaction equation
[C:1]1(=[C:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)[C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.O>C(Cl)Cl>[C:1]1(=[C:8]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:9]2[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 68654371HCID 68654371, compound

Product 1

HCID 11312729HCID 11312729, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (5° C.) solution of 4-{cycloheptylidene[4-(methyloxy)phenyl]methyl}benzonitrile (207) (0.300 g, 0.94 mmol) in CH2Cl2 (20 mL) was added BBr3 (0.358 mL, 3.79 mL). The resultant reaction mixture was stirred between 5° C. and 20° C. for 3 h. Reaction mixture was poured into water (125 mL) and then extracted with CH2Cl2 (3×50 mL). The combined organic layer was dried and concentrated under reduced pressure to afford the crude product. The product was purified by flash column chromatography to give 0.245 g (86%) of compound 208 as a white solid. mp 110-111° C. IR (film): 3391, 2921, 2852, 2229, 1609, 1509, 1213, 829, 731 cm−1. 1H NMR (300 MHz, CDCl3): δ 7.57 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 7.00 (d, J=8.7 Hz, 2H), 6.79 (d, J=8.4 Hz, 2H), 4.97 (br s, 1H), 2.35 (br s, 2H), 2.29 (br s, 2H), 1.60 (br s, 8H). LCMS (ESI): m/z 302 (M−H)−. Anal. Calcd for C21H21NO, C, 83.13; H, 6.98; N, 4.62; Found: C, 83.13; H, 6.96; N, 4.62.

Workup

  1. customThe resultant reaction mixture
  2. customReaction mixture
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. customThe combined organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customThe product was purified by flash column chromatography

Sources & evidence

ORD record
ord-163ec2414cce469c91e1741aaa562f62
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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